


Never the Right Place, Never the Right Time

by AvarieNiceDay



Category: Supernatural
Genre: Canon Universe, Cas Speaking Other Languages, Case Fic, Dad!Sam vibes, Found Family, Human Castiel (Supernatural), Jack being Jack, Light Angst, Lots of Inadvertent Touching, M/M, Mexico, Miscommunication, Mutual Pining, Pining, TFW 2.0, Vacation, Walks On The Beach
Language: English
Status: In-Progress
Published: 2019-09-09
Updated: 2019-11-26
Packaged: 2020-10-13 00:14:01
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 23,729
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20573264
Author URL: https://archiveofourown.org/users/AvarieNiceDay/pseuds/AvarieNiceDay
Summary: The one where Team Free Will 2.0 finally gets the vacation they deserve. That is, until it becomes slightly derailed by a case featuring a monster none of them have ever hunted. Dean and a newly human Cas will be forced to work the case together, and amidst the paradise landscape may just have to face some things they have been avoiding for a very long time.





	1. Chapter 1

**Author's Note:**

> So, this is a canon-divergent story that takes place at a slightly ambiguous time. Jack is around, but powerless, and Cas is human. Make of this what you may. I have a large chunk of the story already written, just waiting to be edited, and I have an idea of how I want this to end but no clue how many chapters it will take to get there. Please, enjoy!

Dean was tense. This was an understatement; Dean was rigid, as if someone had replaced his spine with a steel rod. One might think that a man in his forties may have outgrown such a powerful fear of flying. Dean, unfortunately, had not. 

“This was your idea, man.” Sam teased as he slid into the seat behind his brother. He gripped the back of Dean’s chair and leaned forward to tap his white-knuckled grip on the arm rest. The plane hadn’t even taken off yet; they were just boarding.

“Let’s take a vacation,” Sam dropped his voice an octave in a mockery of his brother. “No monsters, no end of the world crap, just the four of us on a beach with the sun and the sand.” 

“I didn’t think about this part.” Dean replied, jumping slightly when Sam touched him but relaxing his arm fractionally. 

Sam laughed and patted him on the shoulder before slouching back into his seat. 

“So, this machine is going to fly us through the sky?” Jack turned to Sam as he sat back. He had been staring out of the tiny square window, watching workers load their baggage onto the plane. 

“Yeah- don’t worry, Jack. Statistically, flying is actually safer than riding in a car. Dean is just a big baby.”

“At least you have a higher chance of surviving a car crash!” Dean snapped, body turned so he could glare at them over the top of his seat. “A plane goes down and boom! You’re dead.”

“Dean, keep your voice down.” Cas hissed from the seat beside him. He smiled tensely at a young girl with pigtails who had turned to stare with concern at Dean’s outburst. Dean huffed and slumped into his seat. 

“People have survived plane crashes.” Sam started in his ‘I Know Way More Things Than You’ voice. At least that’s how it sounded to Dean. “Though, the middle of the plane is the most dangerous.”

Dean’s neck nearly cracked as he gauged their distance from the front and back of the plane; they were directly in the center. “Son of a bitch.”

Sam pursed his lips to keep from laughing.

“Is that true, Sam?” Cas glanced nervously at Dean, whose fingers were now flexing around his armrest as he took deep breaths.

“Uh,” Sam gave Cas an apologetic look. He hadn’t meant to worry him, just mess with his brother a bit. It was true, though. Sam would never lie about statistics. “Guys, come on. Everything is going to be just fine. People ride on planes every day.”

Cas nodded but continued to dart anxious glances at Dean. He had taken to being a tad overly cautious since the last of his grace had drained away. The knowledge that he could no longer heal Sam, Dean, or Jack was a constant source of worry for him now. If the plane did crash, as unlikely as it may be to happen, there would be nothing he could do to protect any of them. 

“Calm down, Cas. You gettin’ all jittery is just making me feel worse.” Dean had his eyes pressed firmly closed as he blindly laid a firm hand on his friend’s knee to halt its unconscious bouncing.

Cas stilled his leg and took a deep breath, forcing himself to relax. The weight and warmth of Dean’s hand reassured him a bit. He considered placing his own on top of it, just to keep it there, but Dean withdrew before he could act upon the impulse. 

The stewardess began calling their attention to the front of the plane as it started navigating towards the runway. Just as she finished up her safety demonstration and strapped herself into a seat, the plane made a roaring noise as it began to accelerate.

Jack’s wide eyes were glued out the window, thankfully more awed than scared by the experience. Sam craned around so he could watch out the window as well; he really preferred sitting in the window seat, but it was Jack’s first time on a plane. He wanted him to have the full experience. Sam smiled as he watched Jack’s enrapturement, head tilted so close to the window his nose was nearly pressed up against it. 

The mundane scenery surrounding the airport whizzed by faster and faster as they picked up speed. Suddenly, the plane lurched unevenly as it angled into the sky. Dean was jostled in his seat and reflexively reached out to grab something in order to ground himself. He ended up clutching Cas’ forearm in his right hand, fingernails digging uncomfortably into the delicate skin around his wrist. 

Cas looked down at the touch, frowning at the sight of Dean’s calloused fingers wrapped around him. Cas instinctively tried to pry away from the sting of his blunt nails gouging him, wincing as he dug in harder to keep his grip. He looked up at Dean but his eyes were clenched closed tightly, seemingly unaware of the near painful hold he had on his friend. 

It was several long moments before the plane began to even out and steady itself in the air. It was several moments more before Dean finally let out a heavy breath and wrenched his eyes open. He blinked and popped his ears, and as he began to relax his body he noticed his hand wrapped around Cas’ wrist. Cas was frowning down at his arm, eyes gone all squinty. Dean felt a zip of something eerily close to fondness that made him snatch his hand away and rest it in his own lap. 

He grimaced at the little crescent-shaped impressions his nails had left behind and sheepishly ducked his head. “Sorry ‘bout that, buddy.” 

Sam rolled his eyes form behind them. Jack continued to stare out the window as the plane ascended through and above the misty, white clouds. 

“I’m taking down an entire bottle of tequila as soon as we land.” Dean grumbled. 

“Can we not turn this vacation into a booze fest?” Sam interjected, popping his head in-between Dean and Cas’ seats like some kind of PSA puppet. “You said we were going to relax.”

“Tequila is relaxing.” 

“Hangovers aren’t.” Sam countered, fixing him with his patented bitch face. 

“Whatever Sammy, You relax your way, and I’ll relax mine.”

“I want to see the dolphins.” Jack piped in, finally turning his attention away from the scenery outside the window.

“You can swim with dolphins in Mexico.” Cas replied, and Jack’s face practically glowed with excitement.

“I really want to check out some of the Aztec and Mayan ruins,” Sam declared. “There’s a lot of really interesting lore about their cultures.”

Dean coughed ‘nerd’ into his hand and Sam pointedly ignored him.

“They are fascinating structures.” Cas supplied, nodding thoughtfully at the side of Sam’s face.

“You’ve seen them before?” Sam questioned, eyebrows raised in surprise. 

“I have visited most places on Earth. Or, the interesting ones, anyway. The Grand Canyon, the Great Wall, Niagara Falls. They are… awe-inspiring.” Cas grew quiet as his eyes took on a faraway look. 

This had become a frequent mood of his, since he had lost his grace. Whenever he was reminded of his life before- the things he could do and had seen- he drew in on himself. It was the worst the first few weeks after. The mention of anything angel-related would easily throw him into a depressive spiral that locked him inside his own head for hours on end. Cas really didn’t mind being human; in the broad sense of the term, at least. Sure, having to eat and sleep regularly and dealing with common nuisances such as headaches were not perks that he would cite- but, there were bigger things, things he didn’t know how to describe or even really understand quite yet, that seemed to make it worth it. 

But it was difficult to grow accustomed to his new limitations, with the reminder of this wingless form he was now bound to. It had been made apparent to him early on that his new position within the group had taken a steep decline, since Sam and Dean rarely allowed him to tag along on hunts. Recently, he barely got the opportunity to leave the bunker. Thinking back to times when he simply had to stretch his wings and be halfway across the continent… his sudden wanderlust at the mention of the great sights of the world that he had once visited was intense. The restlessness he had been feeling since he fell had really begun to wear on him. Dean may have been the one to ultimately suggest a vacation, but Cas had been subtly hinting at the idea for months.

“Rub it in, why don’t ya?” 

Dean, always so sensitive to others emotions, felt the unease rolling off his friend and immediately jumped to all the wrong conclusions. Sure, Cas missed his wings and the independence his had when he was an angel, but he could find gratitude in his current position as well. Without the ability to always be on the move, he had no excuses to leave and he didn’t mind that. It made the immobility worth it, to an extent.

Dean was always so fixated on what Cas had given up, always convincing himself that he loathed his new life that he never even tried to consider what he had gained; a family, where he finally felt like he was at least beginning to fit in like he should- like he so desperately wanted to. 

Cas sighed, reaching through his conflicting emotions to try and pull out some explanation that would ease Dean’s insecurities. “I miss traveling. I don’t enjoy being cooped up in one place all the time.”

“Yeah, we know.” Dean mumbled. Cas frowned and was about to extrapolate further when the stewardess interrupted them.

“Would you like a drink? We have complimentary Coke products.”

Jack’s eyes lit up as he caught sight of a line of bright red cans perched on her cart. “I’ll have a Coke.”

“Oh, you will?” Sam turned to look at him with a stern expression. “Coke is full of sugar, Jack. It’s not very good for you.”

“Oh for the love of- give the kid a Coke please, darlin’.” Dean hid his exasperation behind a charming smile. “And give me all the alcohol you’re allowed.”

The stewardess blushed brightly and fumbled to pour the soda in a small plastic cup filled with ice. She passed it to Sam, who glared at it disapprovingly as Jack set it on his little tray. 

The stewardess bent over to dig under the cart, Dean shamelessly peered down her blouse and Sam kicked the back of his seat grumpily. She emerged with a large handful of various mini liquor bottles. Dean’s eyes lit up as she deposited them on his tray. 

“It’s a bit more than I’m strictly allowed.” She confessed in a whisper, a shy smile planted on her pretty face.

“I can keep a secret.” Dean promised, voice pitched low and rough, and winked slyly at her. 

“Uhm,” She stammered before turning to address Sam. “Was there anything you wanted, sir?” 

“No thanks, I feel nauseous.” 

She pointed to the pocket in the back of Dean’s seat. “There are bags in there for that, sir… just so you know.” Before pushing her cart along to the next row of seats.

Cas watched her go, deep frown etched into the crease of his brow.

“She didn’t ask if I wanted anything.”

“Did you?” Dean questioned as he deftly twisted off the cap of a small bottle of whiskey.

Cas shrugged solemnly and slumped back into his seat. 

There was a large slurping noise from behind them. Dean turned slowly to peer between their seats, giving Jack a concerned look. 

“This is… really good.” He declared, a pleased smile directed into the fizzy liquid.

Dean scoffed and downed his whiskey in one long gulp before popping off the cap of a mini vodka.

“Is that really necessary, Dean?” Cas asked, voice edged with irritation.

“It’s calming my nerves.” 

“Why don’t you just sleep for a while?” Sam suggested. “If you keep drinking the entire flight, we’ll have to carry you to the hotel.”

“Yeah, yeah. Just one more. To help me fall asleep.” He upended the vodka and immediately followed it with another whiskey. He tucked the remaining three bottles into his pants pocket and stretched out as much as he could in the cramped space.

“Do you think she would bring me more Coke?” Jack stared forlornly at his empty cup.

“See, you’re being a bad influence, Dean. Passing your drinking problem on to Jack.” Sam complained, eyeing Jack’s drink balefully. 

“It’s soda, Sam. Wouldn’t kill you to let loose every once in a while, either. We’re on vacation, have a carb or something.”

“I think Sam may be right, Dean,” Cas interrupted. “You seem irritable. Maybe a nap would help.”

“Fine. I’ll try, I guess.” Dean grumbled, closing his eyes as he leaned his head back. He crossed his arms over his chest and let the white noise of the plane calm him. The three bottles of alcohol definitely helped make him drowsy as well, and before long his breathing became steadier and he slipped into a deep sleep.

It wasn’t until the plane hit some rough turbulence during its descent that Dean was awakened. A particularly hard jolt had him blinking his eyes open in confused alarm. It was through a rough daze that he slowly realized he had slumped onto Cas’ left shoulder at some point during his sleep; his right side was pressed snugly against him, his forehead resting awkwardly, and rather uncomfortably, on his hard shoulder. Cas was incredibly still and tense as Dean carefully righted himself and blinked sleepily.

“We’re landing.” Cas supplied stiffly, his eyes locked out the small window.

“Cool, yeah. Good.” Dean replied, voice scratchy with sleep. He cleared his throat and rubbed his palms over his face and through his hair.

“The stewardess came back around while you were sleeping,” Sam suddenly popped up between them, amused smile stretching across his face. “She wanted to know if you could use a pillow. I told her you seemed pretty comfortable already.”

Dean turned a glare on his brother, flush creeping up his neck. “Funny, Sam.”

Dean tried his hardest to focus on anything but the side of Cas’ face, and the small patch of drool covering his shirt where Dean had laid his head, as the plane touched down and navigated to their gate. Once it came to a shaky stop, the four of them gathered their things quickly and made their way through the airport and down to baggage claim. 

The carousels were full of suitcases, sliding down the chute and plopping into place on the metal belt as they traveled round and round, waiting to be claimed. It was fifteen minutes before the bags from their flight began making their way down, Dean and Sam waiting anxiously to grab them as Cas and Jack looked into transportation to their hotel. 

“I think they have shuttles here.” Cas stated as he looked through the glass doors at the pick-up zone located just outside. 

“The website does say they offer shuttles from the airport.” Jack supplied as he scrolled through his iPad.

Sam and Dean collected their bags, one by one, as they appeared on the carousel and then the four of them made their way outside. 

“Oh,” Jack made a face as they stepped up to the curb. “It’s really hot.” 

Dean snickered and slapped him on the shoulder. “We’re not in Kansas anymore, kiddo.” 

It was a short ride to their resort after they located the correct shuttle. The Sapphire Riviera was a bustling hotel located directly over the water. The four of them had a suite on one of the top levels that consisted of several joint rooms and one large common area with a kitchen and living space. A large floor to ceiling window offered a stunning view of the ocean sprawled out to the horizon. 

Dean let out a breathy ‘wow’ as he stepped up to the window and set down his bag. “Remind me why we don’t we live like this all the time?”

“Because we could never afford this, man.” Sam replied, standing next to him and admiring the view. “We’re just lucky Garth had a connection with one of the managers here.”

“Right,” A slow smile slipped onto Dean’s face as he watched the sun reflecting in the water below like a million tiny diamonds. “I guess it’s the least he could do after Garth saved his ass from those ghouls last summer.”

“It was really driving their business down.” Cas added from behind them.

“Is that the ocean?” Jack asked, slightly breathlessly, as he took in the sight of miles and miles of calm water under the creeping nightfall; like a smooth, dark stone reflecting the blood orange and maroon of the sinking sun.

“It’s so… large.” He pressed up close to the window and looked far left and right down the shore. “You can’t see the end of it.”

“Yes, the Atlantic Ocean is roughly forty million square miles wide.” Cas recalled in his patented monotone.

Dean rolled his eyes and stepped back from the window. “Right, thanks Data.” 

Jack took half a step back so his nose wasn’t pressed against the glass. “I’ve read about it and seen pictures but… this is so much more.”

“Pictures are often a poor substitute for the real thing.” Cas replied absently, stepping back as well to take in the rest of the room.

“Wait till you get down there.” Dean was scoping out the kitchen, his face falling a bit when he opened the full-size fridge and realized it was empty, but smiling when he located a mini-fridge on the bar filled with beer and various bottles of liquor. “The view ain’t as good as it is here, but there’s nothin’ better than sinking your toes in the sand, sitting back with a beer, and listening to the waves.” 

Sam smiled nostalgically, as if this imagery reminded him of something in particular. “You guys hungry? I think there’s a restaurant on the ground floor.” 

“Food sounds good.” Dean agreed, glancing forlornly at the empty fridge again. “I haven’t eaten since breakfast.”

“Alright, let’s get our bags put away and we can get something to eat.” Sam suggested, collecting his bag from where he’d dumped it by the front door.

“There’s only three rooms.” Jack commented, looking pointedly between the three doors adjourning the living room.

“We’ll rotate between the couch,” Dean suggested as he eyed the piece of furniture, sizing it up. “I think it’s even big enough for sasquatch. You can take it the first night, Jack. You’re young and my neck is killing me from sleeping on the plane.” 

Jack nodded in acknowledgement and rolled his suitcase beside the oversized leather couch. Dean, Sam, and Cas dropped their things in the rooms and they all made their way back down to the lobby. Sam had to stop to ask the concierge for directions as he’d left his map they had supplied them with at check-in in the room, and made sure to snatch up several pamphlets detailing all of the different local attractions. 

They opted to take the outdoor path to the restaurant; a route that followed a curving line of cobblestones around the exterior and offered ground-level views of the beach and ocean. They had come at a busy time of year, so there was no lack of tourists, but it was still a strangely peaceful atmosphere. Something about the hot air and darkening skies seemed to stifle and the sound of water pattering over sand rose above the usual noise. 

Jack was increasingly distracted over the view, though definitely not as brilliant at this vantage point, and with the sun sinking lower and lower over the horizon. He tripped over the uneven cobblestones more than once on their way there, almost managing to fall on his face if Cas’ fast reflexes hadn’t righted him in time. 

The restaurant wasn’t exceedingly busy; it appeared that most business was being eaten up by the club-like bar located just down the beach. They could hear the music from their seats on the patio; a thrumming bass that filled the air with palpable vibrations. 

“Tours of the Mayan El Meco ruins near here start at eight in the morning- we could check that our tomorrow.” Sam had spread his pamphlets over the table as soon as they were seated and was pouring over them in interest. “It only takes a few hours, maybe after we could go snorkeling, or take Jack to see the dolphins.” 

“Do we have to have something planned for every second of the day?” Dean grumbled, pointedly ignoring Jack’s visible reaction to the mention of dolphins. 

“There are some really interesting things to see and do here, Dean. Aren’t you at all curious about the local history?” 

Dean gave him a face that clearly stated he was not, in fact, suddenly interested in becoming a history buff. “I just came to relax, Sammy. Sit on the beach and drink some Mai Tais. Work on my tan.” 

The server came around then with their drinks, somehow managing to carry all four without the assistance of a tray. Sam’s eyes narrowed as she sat a large glass of soda in front of Jack. He had obviously been too preoccupied flipping through his pamphlets to notice he had ordered one.

“More soda, Jack?” 

The kid looked up at him with wide, innocent eyes as he loudly slurped the drink through a bendy plastic straw.

“Perhaps it’s alright, just for the week. We are on vacation, Sam.” Cas proposed, fixing Sam with a look that was eerily similar to Jack’s.

“Fine, alright.” Sam relented. “But no one gets to blame me if he develops diabetes.” 

Dean quietly rolled his eyes as he grabbed his beer off the table and slumped back into his chair. They spent the rest of their meal in much of the same manner; Sam discussing sites he was anxious to visit, Jack and Cas intermittently voicing their agreement with certain activities, and Sam periodically fixing Jack’s glass of soda with a glare. Dean watched in contented silence, drinking down his first beer, and then another when the waitress came around and offered him more. 

After finishing their food, they sat in satiated silence for a bit. Enjoyed the distant sounds of the ocean. It had been a long time since any of them had been awarded the luxury of simply sitting and appreciating something so simple, and they soaked it up as much as they could.

“Anyone up for a walk on the beach?” Sam questioned as he stood from the table.

It had grown much darker in the time it took them to eat, but the last few rays of light coupled with the fluorescence glowing from the hotel would award them enough to find their way. 

The patio of the restaurant was situated on the cusp of the beach. They only had to walk down four short steps and take about five more before their sandal clad feet were sinking into the cooling sand.

Sam trudged forward to the shoreline, standing at the fringe and watching the push and pull of the tide as it kissed his feet. Jack came to join him and they began walking along the water’s edge together, hands in pockets.

Cas and Dean hung back a ways. Cas was searching the sand for seashells and Dean felt like taking his time; dinner had made him sluggish, and he was enjoying the view. 

He watched Cas as he walked slowly, eyes cast towards the ground. Eventually he stopped and squatted down, digging into the wet sand a bit and pulling out a shell. He let it wash clean in the water and stood back up. Dean watched as a soft smile curled his lips and he began searching for more.

“Here.” Dean bent down when he noticed something shiny catch the last dimming rays of sunlight next to his foot. He scooped it out of the wet sand and turned it in his palm as he let the water clean it, revealing not a shell, but a smooth stone with a deep blue tint. He held it out to Cas with a small smile.

Cas stared at Dean’s outstretched hand from a few feet away, expression unreadable.

“Uh- if you don’t want it I- I just thought…” Dean stammered, looking acutely embarrassed, arm wavering as he almost pulled it back.

“No, I want it.” Cas moved suddenly, holding his hand out and taking a step closer.

Dean sighed and reached out, upturning the smooth stone into his hand. Their palms and fingers brushed at the movement and Dean was somewhat slow to pull away.

Cas held the stone up to his face between his fore and middle fingers to examine it better in the low light, head cocked slightly to the side. Dean absently noted that the stone was the same shade of blue as Cas’ eyes. After a moment he slipped it quietly into the back pocket of his shorts and smiled widely.

“Thank you, Dean. I like it very much.”

“Uh- yeah, sure. No problem, buddy.” Dean’s turned his flushed face out towards the water and cleared his throat. “Just saw you were lookin’ for rocks.”

“I was actually collecting seashells.” Cas corrected, producing several small but strangely intricate sea shells from his back pocket. One was in the shape of a cone with a complex swirling pattern, another was a typical flat white, but with strange markings covering the inside.

“Oh… cool.” Dean stared at the various shells and pointed to a round, white one. “That’s a sand dollar, right?”

Cas picked up the shell he was pointing to and pressed it into his hand. “It’s the shell of an urchin, really.” He explained.

Dean held the dollar horizontally up to his eyeline, squinting at the thin width. “This is a shell?”

“Yes.” Cas nodded. “Echinoid. These,” he pointed to the five oblong holes riddling the exterior of the shell. “Are pores. They use them to move by passing water through them.” 

“So, it’s not really money?” Cas withdrew his hand from the dollar and looked up at him. Dean was smiling brightly, eyes crinkling at the edges and holding a silent laughter. 

“No, Dean. They have little monetary value. I just find them interesting.” Cas gave him a smile in return and let him press the shell back into his hand.

Cas shoved his handful of sea shells back into his pocket and looked up at Dean again. They were silent for a moment, expressions cast in shadow by the last remaining sliver of sun floating along the distant horizon. The sand under their feet was cool and the water provided a constant white noise that was comforting, almost hypnotizing. 

Dean broke their eye contact when he realized how closely they had drifted towards each other; like unassuming magnets. He looked across the dark water, cleared his throat.

“Hey,” he started, voice cutting through the tension like a hacksaw; jarring and rough. “You wanna go swimming tomorrow?”

Cas tilted his head, expression contemplative as he continued to stare at his friend’s profile. It was becoming harder to distinguish the edges of his form from the rest of the darkness piling around them now, especially when he was turned away from the distant light filtering from the hotel. 

“I’ve never been swimming. I’m not sure if I can.” 

“You don’t know if you can swim?” Dean asked incredulously, turning his face back towards the light.

Cas shook his head slowly as they began walking again. “I never had much need or desire when I was an angel and now… we’ll, I haven’t been out much since I lost the last of my grace. Taking swimming lessons didn’t seem to be a priority.” 

“Right…” Dean ran a hand through his hair, took a breath. “Well, I can teach you- if you want?”

Cas watched him as they continued walking and Dean avoided his gaze. “Okay,” he said eventually, slowly. “That would be… nice.” 

Dean smiled reflexively, pleased. “It’ll be fun. Unless you were wanting to go on that safari tour with Sam and Jack?” 

At dinner Sam had found a pamphlet advertising a local safari tour that boasted a ‘realistic adventure through the jungle’. He’d nearly wet himself with excitement. 

Cas grimaced. “No. I have no desire to ride around in a Jeep through the jungle.” 

“Yeah, I feel you there,” Dean chuckled. “We can relax here all day.” He made a sweeping gesture that encompassed the entirety of the beach around them. “Eat, swim, hit on some hot lifeguards.” Dean winked but Cas just rolled his eyes.

Dean bumped him with his shoulder, smiling as he looked up at him. “It’ll be fun. We’ll have fun.” 

Cas gave him a small smile in return that faltered suddenly. “Oh, I just remembered. I don’t have a swimsuit.” 

Dean waved off his concern. “We can hit up one of the shopping areas in the morning and pick one up for you. They probably have some in the gift shop here,” he glanced over at the hotel for a moment. “But I kinda want to pick up some other stuff, anyway. Like food.” 

Cas nodded and suddenly their quiet conversation was interrupted by an exclamation from Jack, who was several yards ahead of them. 

“What is this stuff?!” He was holding a few strands of seaweed in his hand. “It’s so slimy.” 

“Ew, Jack- put that down, it’s seaweed.” Sam pulled a disgusted face and Jack let the mass plop back to the sand with a wet squelch. 

“It’s starting to get really dark.” Sam commented as he let Dean and Cas draw closer to them. “We should head back and get some sleep.” 

It didn’t take long for the four of them to collapse into sleep once they made it back to their room. Jack was snoring softly on the couch, Sam spread eagle on his stomach in his room. Cas was sleeping fitfully, as he was accustomed to since becoming human, and Dean was having a peaceful dream for a change; the promise of spending the whole next day with Cas on the beach a relaxing prospect.


	2. Chapter 2

**Summary for the Chapter:**

> Dean and Cas spend the day together with only a few hiccups.

**Notes for the Chapter:**

> Heyyy! So this chapter took me way longer than I had anticipated to get edited, but I'm finally done! I promise this fic does have a plot, it's just going to take a little bit to get there :)  
Hope you enjoy!!

Everyone woke at their own pace the next morning. Sam was up first, rising with the sun and setting a pot of coffee to brew in the kitchenette. The sound sound of him puttering around roused Jack from the couch and the two of them sat alone at the breakfast bar for a while, sipping on coffee and munching on dry wheat toast as they waited for Dean and Cas.

Cas shuffled out of his room first, a maroon robe with the hotel’s logo sewn in gold thread over the chest thrown hastily over his pajamas and hair in even more disarray than customary. 

“Coffee.” He grumbled, voice especially gruff with sleep. Sam procured him a cup and Cas sighed in appreciation as he sank into a stool beside them.

“You’re really not much of a morning person anymore, huh, Cas?” Sam remarked, hiding a smirk at his friend’s groggy demeanor behind his mug.

“The idea of needing sleep is still a rather foreign concept to me.” Cas explained, gaining more animation with the caffeine in him. “I might not be getting enough.”

Sam’s eyebrows drew in concern. “How many hours do you get a night?” 

“About two to four.” 

“Geez, Cas. You definitely need more sleep than that. Dean and I can function off that much when we’re in the middle of a hunt or some crises, but it’s not really sustainable. It can start to wear on you if you go too long.” He set his mug down and fixed his friend with a serious look. “You should be getting at least six. Some people need more like eight.” 

“I’ll try to remember that.” Cas replied, glaring sullenly at his coffee.

Dean appeared from his room a few minutes later, looking thoroughly more refreshed than Cas, an extra little pep to him that he attained when he was in a particularly good mood.

“Mornin’.” He greeted them all with a grin before looking expectantly around the kitchen. “What’s for breakfast?”

Jack waved his toast at him and Dean cast it a disdainful look. “I’m not eating dry toast.”

“We have no food here, Dean.” Cas reminded him, frowning over his mug.

“Where’d you get the toast, then?” 

“There was a small breakfast spread in the room down the hall.” Jack replied, mouth stuffed full. “It’s closed now.” 

“Well let’s order some room service, then!” Dean exclaimed brightly, rubbing his hands together. “I could go for some pancakes.”

“You guys go ahead,” Sam started as he stood from his stool and clapped a hand on Jack’s shoulder. “Jack and I are going to head out. The tour bus for the safari leaves at ten, so we’ll just grab something more on our way.” 

“Are you sure you guys don’t want to come?” Jack questioned as he stood to follow after Sam. “It sounds like a lot of fun. The pamphlet said there might be snakes we can actually hold.” 

“Uh,” Dean shuddered before plastering on a wide smile. “We’re good, kid. Thanks.”

Jack turned to Cas who simply nodded in affirmation, before trailing out the front door after Sam. 

“You hungry?” Dean grabbed the room service menu by the hotel phone as he addressed Cas.

“Not particularly.” Cas spoke into his coffee.

Dean glanced up from the menu to the back of his messy head. “Come on, grumpy. You like pancakes, right?”

Cas grunted in reply and drained the last few drops of coffee from his cup. He set it on the counter with a frown.

Dean smiled fondly at him as he crossed the room and gathered up his mug to refill it. He placed it back in front of Cas, keeping his hand wrapped around it until Cas looked up at him. A silent communication passed between them, Dean tilting his head expectantly and Cas letting out a faux exasperated sigh.

“Thank you, Dean.” He rolled his eyes as Dean relinquished the cup and took a long gulp.

“No problem, sunshine.” He returned to the corded phone, picked up the receiver, and dialed the room service number. 

“Hey, yeah, can I get two stacks of pancakes, some fruit, syrup, and like a platter of bacon to room 1102?”

Cas rose from his seat and shuffled across the thinly piled carpet to squint out the large window overlooking the water. They were all so preoccupied with the view below last night, they didn’t realize the floor to ceiling windows actually contained a sliding glass door that led to a small balcony. It was only large enough to hold two two small metal chairs, but Cas pushed the door open and stepped outside. The mid morning air was light and breezy, not yet weighted with humidity. Cas took a deep breath and settled into one of the small chairs, sipping his coffee as he looked over the water. They were up too high to hear it lapping at the shore below, but the sight was still breathtaking in the soft light of the sun peeking over the horizon. He tilted his head so it was partially resting on the high backed chair and closed his eyes.

When Dean finished relaying their food order he turned around to find Cas was no longer in the room. He ran a hand through his short hair and glanced around before catching sight of him through the glass window. Dean crossed the room and paused just in front of the door, stilled by the sight of Cas looking so peaceful; his eyes slightly closed, hands loosely gripping his coffee mug where it rested in his lap. It sometimes shocked Dean how human Cas was now. Especially in quiet moments like this where he would catch him doing something so utterly normal. Before he lost his grace, Cas had already seemed pretty human- at least more than any other angel- but that final bit he had been clinging to really made a difference. Never before had he witnessed him enjoying things like a cool breeze on a summer morning with a warm cup of coffee. 

Dean shook himself as he realized he’d been staring for a bit too long, and quickly moved to join him outside. Cas’ eyes lifted open, just enough to confirm it was Dean who had joined him. Dean crossed the entire width of the balcony in two steps and crossed his arms over the metal railing, leaning up against it to look over the edge.

“Gonna be a nice day.” He commented as he watched the tiny figures of people milling around below them. “We can hit the shops after we eat. Sound good?’

Cas nodded as he stood from his chair to stand beside Dean, resting his forearms on the railing and clutching his mug with both hands over the edge. They watched the bustle of people below them in silence for a beat. Dean shifted his feet, unconsciously inching closer to his friend’s side. After a few moments he took a breath and gently nudged him with his knee. Cas looked up at him expectantly, blue eyes catching the rays of light from the steadily rising sun. 

“I, uh,” Dean stammered. He didn’t have a real reason for touching him, and now his brain was being scrambled by Cas’ sleep hazed, _ really friggin’ blue _ eyes. When the sun hit them like that they flashed with that same incandescence that used to flood them when he used his grace. “I ordered you pancakes.” 

Cas smiled softly and tilted his head, the action taking his eyes out of the direct line of the sun- thank god. He nudged Dean back with his own knee. “Thanks. I am sort of hungry.” 

Dean felt a warmth at the reciprocated contact and smiled back, probably a little gooier than was strictly warranted. He felt drawn in by their closeness- though he felt that way most of the time, but when Sam and Jack were around it was easier to ignore somehow. When it was just the two of them, Dean often found himself drawing in on Cas as if he was stuck in his own personal orbit. He didn’t poke much at the reasoning behind this strange pull he felt deep in his gut; he just knew he wanted to be close to Cas and was often filled with the strangest desire to reach out and touch him for no apparent reason- a hand on his shoulder, an elbow to the ribs, their arms brushing from walking so close together. This feeling was remarkably intense at the moment; watching Cas watch him with his head tilted so slightly, his posture mirroring Dean’s as they leaned with opposite arms braced against the railing. 

Dean started to lift his left hand from his side, but stopped. He had no idea what he was planning on doing, but something told him it may be a bad idea. Cas quirked his brow and smirked faintly at him, but stood resolutely still. 

A knock sounded from the front door and Dean looked to it, then back to Cas. “That’s, uh, probably the food.” He spoke slowly. Cas nodded expectantly, and Dean hesitated a moment before heading back inside to answer it. Cas watched him with a curious expression as he let the hotel employee wheel a cart loaded with pancakes and bacon into the living area. Dean passed the guy a five dollar bill and he smiled appreciatively as he left the room.

Cas took a seat on the couch and Dean plopped next to him after transferring the food from the cart to the coffee table in front of them. He loaded a plate up with fluffy pancakes and smothered them with strawberries, whipped cream, and sticky maple syrup. Cas did the same, but with a much smaller stack and considerably more cream and syrup. He had a bit of a sweet tooth that he tried to limit his indulgence in to times when Sam wasn’t around to scold him. 

Dean was hunched over his plate on the coffee table, shoveling near-whole pancakes into his mouth. Cas cut his food slowly and carefully as he watched Dean inhale an entire strip of bacon.

Dean looked up and caught Cas watching him with a slightly horrified expression. He tried smiling around his mouthful of food. “I’s goo’, mm?” 

Cas chewed his pancake deliberately and nodded. He continued to watch Dean eat as he took a bite of strawberry.

“Why do you always eat like that?”

Dean swallowed hard and narrowed his eyes. “Like what?”

Cas was quiet for a moment, trying to choose his words carefully. He didn’t want to offend his friend, but he had noticed, especially since becoming human, that Dean seemed to eat in what most would consider a less than civilized manner.

“Like you haven’t eaten for a week, I suppose. I went without food for a week when I was human human- before- and I imagine the first meal I ate was in a similar manner.” Cas explained, pointing his fork at Dean’s nearly empty plate beside his practically full one.

Dean frowned down at his food and pushed the last few bites around his plate thoughtfully. “You got a problem with the way I eat, Cas?” He’d meant to sound accusatory, but it came out more solemn.”

“Not at all,” Cas replied quickly. “I’m just curious.” He shrugged, taking another bite of food and chewing it thoroughly. “I’ve just noticed other people eat more slowly. I don’t know what’s considered normal, really.”

Dean stared at Cas blankly for a long moment before returning his gaze to his plate. He shrugged, shoved his last bite of food into his mouth, and relaxed back onto the couch cushions.

He remained quiet for a while and Cas figured he wasn’t going to get a real answer as he continued eating the rest of his food. He was nearly finished when Dean finally spoke again- quiet, and with a faraway look in his eyes as if he was remembering something.

“We didn’t have much food around when I was a kid.” 

Cas set his fork down and leaned back beside him, body turned toward Dean to show his silent attention.

Dean continued to stare straight ahead at seemingly nothing. “When dad would go off on a hunt and leave Sammy and me in a hotel room for weeks on end, sometimes we ran out. I could steal little things… packets of ramen, some hot dogs, granola bars from a gas station- but that didn’t get us far. Sam seems all tough now, but he was a whiny little shit of a kid and he would complain about being hungry and I just couldn’t bare to watch it. I was in charge of him, ya know? A lot of the time I would go without a single real meal for days.” He crossed his arms unconsciously over his chest and shifted further into the couch. “When we stayed with Bobby or some random hunter friend of dad’s it was a relief to know I’d have something to eat at every meal- though Bobby was a shit cook.” He smiled to himself. “But baked beans from a can and ham sandwiches were better than stale saltine crackers and a handful of mints from a motel lobby.” He shook his head suddenly and focused his eyes on Cas, as if suddenly remembering himself. “So, I guess that’s probably why.”

Cas held his gaze steadily, trying to think of something to say. He had been aware of some of it, obviously, but he had never heard Dean speak so openly about his childhood, let alone his own perspective of it. It was heartbreaking, really, to know that even thirty years later he was holding onto that trauma- that he may not be guaranteed another meal, no matter what his current situation in life was, so he ate as much and as fast as he could.

“I’m sorry, Dean.” Cas spoke quietly, still holding his gaze. “I didn’t mean anything by it when I asked, I was honestly just curious.”

Dean shrugged and gave him a self deprecating grin. “S’no big deal. Guess I’d just never really thought about it much before.” 

“Thank you for sharing it with me.” 

Dean sat up suddenly and clapped a hand on Cas’ knee before standing. “Well, we should get going. Let’s get changed and we can head down to the markets.” 

Cas watched Dean as he retreated to his room and closed the door before letting out a heavy sigh. All things considered, he counted this as a win. Getting Dean to talk about anything even slightly emotional was usually tantamount to some acute form of torture. This had been fairly voluntary- Cas hadn’t pushed for anything and hadn’t really considered the fact that Dean’s eating habits stemmed from his messed up childhood. He had honestly thought it was simply one of Dean’s many quirks that made him so endearing. He never would have imagined it was rooted in such trauma. 

Cas ran a hand through his already messy hair and stared at Dean’s closed door. Even if he did close himself off immediately after, he had succeeded in wedging a tiny crack in that ever present stoicism and pulling a bit of emotion from him. Cas wasn’t sure why, but this had become an increasingly desperate mission of his since becoming human. Getting Dean to open up to him made him feel important, it always had, but now it seemed more significant. Dean was placing his trust in him, letting him see his most vulnerable attributes and this was something Cas found nearly addictive. He supposed he enjoyed feeling needed and often tried to explain it away as such, but it seemed to only revolve around Dean. Sure, he was always happy to help Sam and Jack, and even Mary if she came to him for something, but it was just different with Dean. Cas was learning that most things were. 

His mind continued to wander as he gathered up their dirty dishes and piled them back on the cart. He wheeled it outside their door to be collected by the cleaning staff and retreated to his own room to get changed. After pulling on a pair of shorts and one of his tighter-fitting shirts- one he would have discarded by now if Dean hadn’t once off-handedly mentioned that it ‘brought out his eyes’ (though he wasn’t entirely sure what that meant, he supposed it must be something good since Dean was smiling when he said it)- and met Dean back in the living area.

Cas fixed Dean with an incredulous look as he took in his outfit. He was wearing a bright green button up hawaiian shirt with little blue flowers on it. He held his hands out in front of himself and raised his eyebrows at Cas.

“Whaddaya think?” 

Cas inhaled, blinking rapidly. “It’s very, er, bright.” 

Dean rolled his eyes and fiddled with one of the buttons self-consciously. “I like it… it’s festive.” 

Cas took a step closer and clapped a hand on his shoulder, gaining his attention. “It is very festive. I like it- I’ve just never seen you wear something so colorful.”

Dean blushed faintly and shrugged. “Thought I’d get into the spirit, ya know?” 

“Is this typical attire for this environment?” 

Dean chuckled. “It’s more of a tourist thing, really. I mean, we’re not in hawaii, but ya know, same general principles.” 

Cas contemplated this for a moment. “I’ve never heard of this tradition before- should I have one, too?” 

Dean laughed. “Sure, buddy. I’m sure they have some at a souvenir shop around here. We’ll pick you one up.” 

They made their way to the lobby of the hotel and were able to hail a taxi outside fairly easily. The closest market was only a few miles away so after a short ten minute ride, they were being dropped off and Dean slipped the driver some pesos for a tip before exiting the car. 

The street they stepped onto was covered in cobblestones and lined with an array of vibrant and eccentric open store fronts. Many appeared to be dedicated to selling kitschy souvenirs, a few boasted large and fragrant fruits and veggies lined in wooden crates, and others sold clothes and other travel necessities that one may need to pick up; sunscreen, flip flops, sunglasses, etc. It was still fairly early in the morning so the crowd was thin, mostly older couples perusing the souvenir shops and some locals purchasing produce. 

Cas felt vaguely overwhelmed by the variety of options and bold colors, so Dean grabbed his elbow and steered him towards one of the produce stands. 

“Let’s look for some food.” He suggested, pulling down an empty crate down and looking over the oranges. “We don’t need much, I don’t mind eating out. But Sam will be happy to have some health food, and it’ll be nice to have some things up in the room.”

Cas nodded and picked up a large papaya. “I don’t think I’ve ever had one of these.” 

Dean plucked it out of his hand and placed it in the crate. He also grabbed some apples, bananas, a head of lettuce, some cucumbers, and a large watermelon. 

“I think Jack once said he likes these.” Cas supplied, picking out a few peaches and adding them to the rest. 

“Alright,” Dean looked down at the now incredibly heavy container, shifting it in his arms to get a better grip. “That should be good for a few days at least.” 

They made their way to the store front and paid the shopkeeper. Dean shifted the crate in his arms again, looking slightly uncomfortable under the weight.

“Here, let me help.” Cas reached forward to grab one side and they held it between them, each holding up one side of the crate.

“Thanks, man.” Dean gave him a smile and looked around as they entered the street again. “Alright, now let’s find a place that would sell swimsuits.”

After scanning a few other stores he motioned with his free hand down the street a bit. “Here, this way.” 

They walked together, crate hanging between them, to a shop with a handmade sign out front that read: Ropas, Gafas de Sol, Joyeria, Zapatos, y Mucho Mas Aqui! 

Inside, there were rows and rows of souvenir t-shirts, handmade jewelry, an entire wall of different colors and sizes of sandals, fridge magnets, bottle openers, shot glasses, and a plethora of other souvenir knick knacks. Cas even found a button up shirt similar to Dean’s but in blue and red. Dean snatched it up before leading them to the very back of the store, where there was a large rack of men’s and women’s swimsuits. 

Dean sat the crate down by their feet and gestured vaguely in the direction of the men’s half of the rack that featured mostly knee length shorts and, though he tried not to think about it too hard, a few more risque speedo-type suits. “You, uh, just pick something out. I’m gonna look around- I forgot to bring sunglasses.” 

Cas nodded absently as he contemplated the different options available to him. Dean sauntered off to the front of the stop where there was a turn-table style display of sunglasses. He absentmindedly spun the display, picking up a pair occasionally and ducking slightly to view his reflection in the tiny rectangular mirror affixed to the top. He’d narrowed it down to two different pairs when he heard Cas calling for him from the back of the shop.

“Dean?” He called again, sounding anxious. Dean followed the sound of his voice to the back of the shop.

“Cas?” He called out, when he reached the rack of swimsuits and the crate where he had left it on the floor.

“In here.” He heard, voice drifting from behind a curtain tucked away in the corner of the shop, just a few feet from the rack. Dean realized it was a makeshift changing room as he approached it, the thick green and red fabric rustling slightly where Cas stood behind it.

“What’s goin’ on, man? Did you find something?”

“Uhm,” Cas’ voice wavered uncharacteristically. “I don’t know. There’s no mirror in here.”   
  


“Yeah, so?” Dean replied, brow furrowing in confusion. “Just pick a pair, it don’t matter what they look like, Cas.”

“I wanted to make sure they fit right. I’m not sure how normal pants measurements translate to ‘small’, ‘medium’, and ‘large’. Those are usually just shirt sizes.”

Dean ran a hand over his face, equal parts frustrated and guilty. He should have explained that to Cas. “Yeah, okay. Come on out, lemme see.” 

There was no movement from behind the curtain for a solid ten seconds. Then, Dean could hear Cas taking a deep breath and saw his fingers curl around the edge of the tick fabric before easing it open. Once it was open enough to reveal himself, he took a step back, further into the alcove, and crossed his arms self consciously over his chest, face fixed on the ground by his feet. 

Dean could admit it was weird to watch Cas looking self-conscious over anything, though it was something he was growing more accustomed to since he became human. As self-assured as he usually was as an angel, being human was new to him and lent itself to much embarrassment when Cas didn’t understand basic human interactions or nuances. 

As it was, Dean rubbed the back of his neck awkwardly and let out a quiet breath. Cas had picked out a pair of light blue shorts with waves on them; fairly conservative, really, as it seemed he had chosen a pair that were about a size larger than what he actually needed. They hit just at his knees, sagging slightly at his hips. He had left his slightly-too-tight blue shirt on and just looked like he was wearing a normal pair of shorts, honestly. Dean let out a small chuckle; really he was just relieved the guy hadn’t picked out one of the speedos. 

“They’re fine, Cas.” He reassured. “Maybe a little big? What size are they?”

Cas shrugged and twisted his upper body, trying to locate the tag on the back waistband. “I can’t remember which size I settled on. It was confusing. I just liked this pattern. Is swimwear typically tighter? I know women’s are, but…”

Dean stepped forward, catching his attention and motioning for him to turn around. “It depends really. Yeah, most women prefer to wear tighter swimsuits ‘cause otherwise the material can get water logged and make it harder to move in the water. There’s options like that for guys too,” He tugged slightly at the waistband of Cas’ shorts, “but most are like this.” 

Cas sighed and fidgeted anxiously, looking over his shoulder as Dean carefully flipped the elastic waistband over to pull the tag out. He clicked his tongue. “Yup, these are an extra large, Cas. The size pants we normally get you are more like a regular large.” He reached up to pat him comfortingly on the shoulder, but was distracted by a noise behind them.

“Uhh.” Dean turned to see a woman stopped a few feet away from them, a pink and blue tie-dyed shirt clutched in her hand. Dean looked back up at Cas and at once realized how close they were, how his hand was still holding the elastic waist of his shorts, and what it must have looked like to someone else. 

“I’m sorry, I just-” the woman blushed and turned away, holding the shirt in front of her like a shield. “Just wanted to try this shirt on.” 

Dean quickly let go of Cas and held his hands up imploringly. “No, that’s-” he sputtered unhelpfully before placing his head in his hands and letting out a loud sigh.

“I’ll just, uh… I’ll use the one up front.” And she turned sharply on her heel and booked it for the front of the store.

“Jesus.” Dean shook his head in embarrassment, face heating up as he watched her retreat.

“Why was that woman acting so strange?” Cas questioned from behind him, squinting after her as well. Dean kept his eyes on the floor.

“Just- get your pants back on and find a smaller suit.” He demanded, though his voice came out a bit more strained than he planned. 

Cas cast one last questioning glance at the side of Dean’s face before shrugging and gripping the edge of the thick curtain, closing it with a loud swish.

Dean was waiting for him at the front of the store, fingers tapping restlessly against the crate he had gathered from the floor and set on the checkout counter. He paid for Cas’ swimsuit and the hawaiian shirt they had found quickly, speaking only in grunts, and ushered Cas out of the store.

Cas grew frustrated as Dean’s bad mood persisted all through the drive back to the hotel, after dropping off the food they purchased and changing into their swimwear and plain t-shirts to go down to the beach. Cas was familiar with Dean’s brooding silences, but he could not for the life of him figure out what had set this one off. 

“Dean,” Cas was practically jogging to keep up with him as they strode down the boardwalk to the beach. He had been trying to coax small conversation out of him since the cab ride back to the hotel but Dean was proving to be as resolutely stubborn as ever. “Dean!” 

Cas sped up and clapped a hand on his shoulder, spinning him roughly round to face him. 

“What the hell?” Dean grunted, giving him a light shove to increase the distance between them from the maneuver. 

“Yes, ‘what the hell’, Dean?” Cas parroted, fixing him with an annoyed glare. “You’re acting very strangely and I don’t understand why.” 

Dean crossed his arms over his chest defensively and looked away. “Sorry, Cas.” He heaved a resigned sigh and let his arms drop to his side. “That chick just…” 

“The woman at the market?” Cas clarified, still confused. “Will you please explain this to me, Dean? Sometimes these human social interactions completely baffle me. It’s insanely frustrating.”

“Okay, okay,” Dean rolled his eyes but his cheeks were heating up again. “She was just being stupid… jumping to conclusions.”

Dean shifted from foot to foot under Cas’ gaze. “What conclusions, Dean?”

“Uhh,” Dean ducked his head and rubbed the back of his neck self consciously. “Whaddaya think, Cas? I mean- we were shoved in that tiny little alcove with my hand practically down your pants.” 

Cas’ eyes narrowed before going wide with realization. “Oh. I see.”

“Yeah.” Dean squeaked, eyes still evading Cas.

“That would not have been a very convenient place to attempt to fornicate.” Cas ruminated, looking thoughtful. “The space was very tight, and somewhat public.” 

He tried not to dwell on the thought that Dean seemed agitated by the thought of this random woman assuming that they were engaging in such activities. That was obviously the underlying cause of his distress- not that this woman thought Dean was capable of engaging in such public acts, but that she thought he was capable of engaging in them with Cas, specifically.

Dean sputtered out an embarrassed laugh.”Yeah, I guess you’re right. Though… some people don’t exactly mind that.” 

“The public part?” Cas questioned as they resumed walking along the beach. The day was well on its way now, sun hanging hot and heavy above them and tourists quickly filling the beach to take refuge in the cool ocean water. 

“Uh, yeah.” Dean replied, trying to shrug nonchalantly but only managing to make it look like anxious twitch. “Just one of those things.” 

“One of what things?”

“Ya know.” Dean gave him a look Cas had grown accustomed to since becoming human- like he should intuitively understand what Dean was saying.

“No, I don’t.” Cas persisted, annoyed. “My experience in anything sexual is woefully lacking.” 

“Right,” Dean continued, looking vaguely surprised. “So, just April, then?”

“Yes.” Cas intently watched the way his feet kicked up the sand as they trudged through it. “And it’s not as though I have many options holed up in the bunker, Dean.” 

Dean bit his lip as he kept his pace beside him. “Yeah.” He stopped abruptly, about fifty feet from the water. “Let’s put our stuff here.” 

Cas sat his bag he had packed with various necessities on the ground and pulled out two towels. “What did you mean, though?” 

“Hm?” Dean took his towel and laid it out before searching through the bag for his sunscreen. “Oh, about doing it in public places?” He kept his focus on rummaging through the bag, forcing down the intense anxiety he felt from breeching such a subject with Cas. He couldn’t understand it- he had powered through all kinds of uncomfortable topics with Sam when they were growing up. With Cas it was different, for whatever reason. Trying to explain exhibitionism to his newly human, vastly inexperienced, best friend was in a league of its own. 

“It’s like- like a kink.” Dean found the sunscreen, holding it lamely in his lap as he watched Cas’ large hands smoothing his towel over the sand. Dean quickly busied himself with opening the bottle and slathering lotion over his arms. 

“A kink?” Cas tilted his head and sat cross-legged on his towel. 

Dean had purposefully picked a sparsely populated section of beach to park their things, but he glanced around nonetheless and lowered his voice.

“Yeah, like, something that gets you going.” 

“Get’s you-”

“Oh my god- something that turns you on, makes you hot- whatever.” He snapped and tossed the sunscreen with a bit more force than necessary into Cas’ lap.

Cas caught the bottle on reflex and stared at it solemnly. 

Dean took a deep breath and willed his embarrassment away. It wasn’t Cas’ fault he didn’t understand some of the weirder nuances of human behavior. It also wasn’t his fault that Dean seemed to be devolving into some blushing schoolgirl.

“Dude, just- watch some porn sometime or something, I don’t know. Educate yourself.”

“Right.” Cas nodded to himself as he opened the bright orange bottle and began rubbing the sunscreen into his arms.

“Don’t forget your chest and back,” Dean supplied, his mother hen instincts taking over. “Sam did that once- forgot to get his back. Had to sleep on his stomach for a week.” 

Cas peeled his shirt off and folded it on his towel. 

“Where’s the liquor?” Dean lounged back on one elbow and used his other hand to shield his eyes from the sun as he scanned their surroundings.

“There’s a cabana over there serving beverages.” Cas nodded to their right as he squirted more lotion onto his palm and began rubbing it over his chest.

Dean was slow to follow where he had gestured as he found himself inexplicably interested in Cas’ hands moving over his chest and stomach.

“Ah,” Dean exclaimed when he finally looked away and squinted across the beach. “I’ll be right back.” He rose with only a small amount of difficulty and creaking knees, and slipped his feet back into his sandals. “You want anything?”

Cas looked up from his hands gliding over his skin. Dean gulped.

“Sex on the beach?”

“W-what?” Dean stammered, brain moving sluggishly as he tried to restrain himself from glancing below his friends eye line. 

“Isn’t that what it’s called? I heard a woman order one at a bar once. It looked… interesting.”

“Oh! Oh, yeah. They’re good. Fruity.” Dean bit the inside of his cheek at his stuttering speech and looked away. “I’ll get you one, ok?” 

Cas nodded and Dean made his way to the cabana. He took one shot on the spot, for his unusually twitchy nerves, and carried a beer and the fruity drink back to Cas. He seemed to be finished with the lotion (thank god) so Dean made a little hole in the sand for his beer and pulled his shirt off to get his own chest and back before chucking the orange bottle back into the bag. 

“When are we going to get into the water, Dean?” Cas questioned as he sipped his drink. 

“In a bit,” Dean replied, waving a hand lazily through the air. “Drink your drink and just relax for a minute.” He took a long pull from his beer bottle and laid all the way back on his towel. 

Cas remained in a stiff, cross legged position on his towel, continuously sipping his drink. 

“You like that?” Dean asked, squinting up at him from his lower position. 

“It’s very good.” Cas admitted, using his straw to stir the now half empty contents. The straw was bright pink and there was a red and yellow umbrella peaking over the rim of the cup. Dean remembered a time when he would have poked fun at his friend for ordering something so girly. A time when he was a bit less secure. Not that he was the height of self confidence now, but life had managed to teach him at least a few things over the years. 

“Can I try?” Dean asked suddenly, pushing himself up a bit and reaching a hand out. 

Cas looked at his outstretched arm for a moment before nodding and handing the plastic cup over. 

Dean debated over the pink straw for a minute before pinching it out of the way and drinking straight from the cup. “Shit.” He declared, licking his lips as he stared at the drink. “That’s pretty fucking good.”

Cas fixed him with a broad smile as he took it back. “Much better than beer.”

“I wouldn’t say that.” Dean replied, taking another swing of his own. Cas smirked at him. 

They sat in comfortable silence while finishing their drinks, watching the beach become steadily more crowded as those who were nursing hangovers from the night before finally arose to greet the day. The sun was hanging almost directly overhead and hazy in the humid heat, imbuing a sense of laziness in the mass of people gathering on the beach, and creating a rather subdued atmosphere. Nothing like it would be later that night, after the sun slipped away and the cool air revived them. The bar a ways down the shore would open and blast loud music for the whole beach to hear.

“Alright,” Dean pushed himself up until he was sitting with his legs sprawling in front of him. “You ready?”

Cas nodded and they stood together. 

“Let’s go over this way.” Dean suggested, leading him several yards away to the edge of the water. 

“So,” Dean placed his hands on his hips, looking out over the water as he thought. “I mean, how comfortable do you feel in the water?”

Cas shrugged. “I’ve never taken a bath.”

Dean let out a chuckle. Cas rolled his eyes. “I mean I’ve only ever used a shower.” 

Cas grew quiet for a moment as he stared down at his feet, the waves barely tickling his toes in the wet sand. “The only time I’ve been submerged in water was, well- the leviathan.” 

“Right…” Dean replied, fixing him with a worried look. “Does the thought of being in water make you anxious?”

Cas contemplated this question and swept his eyes over the water’s sprawling surface. “I… don’t think so.”

“Well, that’s good.” Dean gave him a toothy smile that he couldn’t help but return. “Look, we’ll start small, okay?” He took several steps into the water, until it was up to his knees, and motioned Cas to follow him. He did, swiftly. Dean smiled encouragingly at him and took a few more steps, until the water was nearly up to his waist. Cas trailed him, watching the water rise up over his swim shorts and stop just at his hips. 

“Okay, how’s this?” Dean questioned, hands gliding on the surface of the water as he turned to face him. 

“Fine.” Cas replied. Then, a surge of water came towards them; remnants of a larger wave out in the open water drifting to shore. It wasn’t strong, but it was enough to have to brace against, which Dean did instinctively. Cas, on the other hand, was completely unprepared for it and began to lose his balance as the water rippled around him, small waves crashing into his stomach. 

“Woah!” Dean exclaimed, reaching out to clamp a wet hand on his arm to steady him again. 

“I didn’t like that.” Cas declared, looking at Dean with wide eyes after the waves had passed and he felt stable again. 

“Just waves, Cas. It’s a bit harder to do this in the ocean compared to a swimming pool. A bit less of a controlled environment going on here. But, you’ll be fine.” He gave his arm a tight squeeze before letting him go and taking a half step back in the water. 

“I think the first thing you should do is go underwater. Like, dunk yourself.” Dean suggested, crossing his arms as he considered. 

“Okay.” Cas replied. “I think I can do that.” 

He bent his knees until they were resting on the sandy floor, the water halfway up his chest now, and slowly dunked himself under. He stayed under for a few seconds before breaking the surface again, sputtering and spitting water out of his mouth. 

“Uh- you know humans can’t breath underwater, right Cas?” Dean joked as he slapped him on the back during his coughing fit. 

Cas fixed him with a wet glare. “Yes, Dean. I just didn’t realize how easily it would go up my nose. And then I panicked and opened my mouth.”

“Oh, right.” Dean gave him a sheepish smile. “Some people find it easier to pinch their nose closed, or just continuously blow air out while they’re underwater. Shoulda mentioned that.”

“Maybe I should wait and consult a professional to help me with this.” Cas said wearily. 

“No, no! You’ll be fine. I mean, I did teach Sammy how to swim. It’s just a bit different ‘cause you don’t have a natural intuition with human biology or whatever.” 

“You taught Sam to swim?” Cas repeated, looking interested by this fact. 

“Yeah!” Dean’s face brightened at the memory. “He was like seven. Dad put us up in a motel with a pool… not the most hygienic place, but it definitely helped motive Sam from accidentally inhaling any pool water.”

“Alright.” Cas acquiesced. 

“So, try to go under again. Only this time, maybe pinch your nose closed. Also, don’t open your eyes ‘cause this is salt water and it’ll sting real bad.”

Cas readied himself, this time with thumb and forefinger holding his nose closed, and dunked under again. He came back up smoothly and pushed his wet hair out of his eyes, smiling. 

“Great!” Dean beamed. “Now let’s try to float on your back.” 

Dean demonstrated how to maneuver onto his back in the water; arms out, ears under the surface, lungs filled with air to help float, hips pushed forward. Cas watched him carefully, and when Dean was finished he laid back in the water and attempted it for himself. 

“Right, good job.” Dean spoke softly as he stepped closer. Cas’ stomach began to dip under the water and Dean reached out, gently pushing his back up to keep his hips tilted towards the sky. 

They stayed like this for a few moments, Cas figuring out his balance in the position and Dean adjusting certain things as necessary until he had it down. 

“This is… peaceful.” Cas murmured, staring up at the sky as he floated. 

“Yeah. When I was a kid I used to love floating in a pool.”

Cas smiled. After a few minutes they moved on, Dean demonstrating how to tread water and proper breathing while doing a breaststroke. It took Cas a while to catch on; he flailed wildly at first when attempting to move his arms and legs in synchronization. Eventually, he got the movements down. He definitely wasn’t about to win any Olympic medals, but he could get from one point to another… eventually, and with many stops to recoordinate himself. 

It was nearly noon by the time they decided to finish their lesson. 

“I’m getting tired.” Cas admitted as they were treading water that was just deep enough for them not to touch the bottom. 

“Yeah, all this teaching is making me hungry. Can you make it to the shore on your own?”

Cas was kicking his legs to tread water, his arms moving just under the surface. He began moving his arms more broadly, trying to propel himself forward. It worked, but he was moving very slowly. 

“You can’t get face down in the water that way?”

Cas floated forward, trying to kick his legs up closer to the surface, but his balance was just not there yet. “It’s much harder without the ground to push off of.”

“Yeah, that’s fair.” Dean swam closer, pulling one of his arms around his neck. “It’s easier to do in a pool… you can push off the sides and there aren’t many areas that are too deep to touch down.” 

Cas secured his arm around Dean and felt his side being gripped. He stiffened slightly, but Dean gave him a reassuring squeeze. 

“Just gonna get you to where you can reach.” 

Dean used his free hand and legs to propel them towards the shore. It was slower moving trying to haul Cas, but they hadn’t traveled far from the shore. 

“Should be able to reach here.” Dean put his feet to the ground and was able to stand with his neck and head still out of the water. Cas did the same, though the water came just a bit higher on him, and after a beat they untangled their arms from around each other. 

“Thank you, Dean.” Cas gave him a warm smile as they made their way to the shore. 

Dean dug his cell phone out of the bag when they got back to their towels and noticed a text from Sam. 

“Hey,” Dean waved his phone at Cas, who was pulling his shirt back over his head. “Looks like Sam and Jack just finished their Safari. They want to meet for lunch.” 

**Notes for the Chapter:**

> Please let me know what you thought- it would really mean a lot :)  
Thank you!


	3. Chapter 3

**Notes for the Chapter:**

> Ok so I guess I'm super slow at editing- sorry chapters take so long for me to get out! This was supposed to be a huge ass chapter that I ended up breaking down because it would have taken me forever to finish. Sometimes it takes me a bit to get into the groove of a story and I feel like I hit it towards the end of this chapter. 
> 
> I feel like it's taking a long time to get to the main plot/case of this fic, but it's coming- I promise! 
> 
> Oh, also, I took like five years of spanish in high school but am in no way fluent in the language, so I apologize if there are any grammar mistakes or the language used sounds off. 
> 
> Thanks so much to those of you who have left kudos/commented so far, I appreciate it and it motivates me to get things done faster :)  
Enjoy!

There was a restaurant about half a mile away- just off the invisible boundaries of their resort, but still abutting the beach- that Sam suggested they meet at. Dean and Cas took a moment to dry off and pull their shirts back on, but not much could be done about their water logged shorts.

“Should we go change first?” Cas asked, attempting to wring out the leg of his swim suit as best he could. When he figured they were as dry and they would get, he sighed and ran a hand through his damp hair, causing it to stick up in all directions. Dean chuckled as he reached out to flatten the mess down. 

“Nah,” he started, leading Cas along the boardwalk. “Restaurant on the beach has to be used to soggy customers.” 

It was a short walk for them, but the- now intense- heat of the sun managed to evaporate most of the water still clinging to them by the time arrived. After looking around briefly, they realized Sam and Jack weren’t there yet and requested a table on the open patio round the back. It was a large, deck like structure with creaky wooden panels lining the floor and providing an elevated view of the beach and water beyond it. Flowery umbrellas dotted each table, some opened to shield customers from the sun and others tightly folded for those looking to improve upon their tan. Dean blinked at the colorful menu the hostess handed him as they sat down, the laminated front page of which featured a cartoon of a bright red crab smiling up at him.

They had only been sitting for a few short moments when a pretty girl with long, black curls and a pink apron tied precisely around her petite waist approached their table. Her teeth were perfectly white, accented by her maroon painted lips, and her dark brown eyes held a comforting depth and warmth that intensified when she smiled.

“What would you like to drink?” She asked, thick accent dripping over her words like honey.

Dean looked up from his staring match with the crab and his face reflexively dissolved into a charming- if slightly leering- smile as he let his eyes wander slowly up and down her body.

“I’ll have a beer, sweetheart.” He spoke, voice pitched slightly lower than usual in obvious and shameless flirtation.

“Right.” She frowned at his overt approach, barely suppressing an eye roll, and turned her gaze to Cas. “And for you?”

Cas turned narrowed eyes from Dean to the waitress before rearranging his features into a small, shy smile.  _ “Disculpe mi amigo, siente la necesidad de ejercer su virilidad alrededor de mujeres atractivas. Si quieres enseñarle una lección, tráele la bebida más frutal que tengas. Tendré lo mismo.” _

The woman’s tight and defensive body language quickly disappeared as she giggled, making a quick note in her serving pad. “It’s okay, for every  _ gilipollas _ , there is a  _ bombón _ that makes up for it.” She gave him a wink before turning on her heel to go get their drinks.

Dean watched the entire exchange with consternation, face twisting into a confused snarl. As soon as she was out of ear shot, he leaned across the table with an accusing glare.

“What the hell did you say to her?”

Cas shrugged nonchalantly as he opened his menu. “I thought I would attempt a flirtation.”

Dean stared at him, open mouthed, for a good ten seconds. “You were trying to flirt with her?”

Cas glanced up from his menu. “Is that not customary when you find someone attractive?” He raised a teasing eyebrow. “And I think I was succeeding, rather than just  _ trying _ .”

Dean internally flailed, mouth opening and closing three times before finding any useful words. “Well, yeah- I guess so. It’s just-  _ you’ve  _ never done that before. Ever.” 

“You’re the one who’s always telling me I need to act more human,” Cas pointed out, still looking down at his menu. “I’m just trying to follow your lead, Dean. Besides, weren’t you just telling me I should… educate myself?” He caught Dean’s eye and his brow ticked up. “Thought I’d give it a go.”

“Right,” Dean replied quietly, breaking eye contact to stare at the wooden tabletop. “Yeah… of course.” 

Cas sighed, taking a moment to wonder over the hypocrisy of his friend. Dean was flirting- albeit in a rather juvenile manner- with the waitress at first, but it became an issue when he attempted to turn the situation on him? Cas was about to say something more to him when Jack and Sam appeared. 

“Hey, guys!” Sam greeted, sliding onto the bench seat next to Dean and shifting him down the table a bit. Jack took the empty spot next to Cas, immediately reaching over him to grab a menu from the table caddy.

“I am starving.” He exclaimed as Cas smiled at him.

“Hello Jack, Sam.” Cas replied. “How was the safari?”

“It was so awesome!” Jack proclaimed, face split with a wide smile. “Show them the picture, Sam!”

Sam chuckled as he pulled out his phone and scrolled through his pictures, selecting one and turning the screen so Cas and Dean could see. The image was of Jack, standing in a large clearing with four other people. One must have been the safari guide as she had a radio clipped to her shoulder and was wearing a cheap, red hat with some company logo on it. She was standing stoically to the left of a man wearing thick rubber gloves and keeping a watchful eye on Jack and the giant reptile encircling his neck and shoulders. It’s body was thicker than a coke can, and its glittery scales formed a black and brown pattern all down its long body. Jack was smiling toothily at it as it wound around both his shoulders and down his right arm.

“Holy  _ shit ,  _ is that real?” Dean exclaimed, snatching Sam’s phone out of his hand so he could examine the picture more closely.

“Sure is!” Jack declared.

Sam extracted his phone from Dean’s hands and slipped it back into his pocket, ignoring the slightly repulsed expression on his face. “It was really cool, actually. We got to see a lot of indigenous wildlife up close.”

The waitress returned to their table then, carrying two tall, frozen drinks filled with various fruits and a little pink umbrella resting against the lip of each glass. Dean stared at it in confusion as she set it in front of him.

“Uh- I don’t think-” 

“Oh, your friend said this was what you preferred but you were too embarrassed to ask for it.” 

Cas snickered into his own drink, and smiled up at the waitress. “Thank you, I’m sure he’ll love it.”

“No problem.” She replied, smiling beatifically back at him. They both ignored the affronted look Dean was shooting at them, so he set to glaring balefully into the pink slush of his beverage.

“My name’s Cas, by the way.” Cas offered after a moment, as she was still looking at him.

“Isabel.” She replied, tucking a stray strand of hair behind her ear in an almost sheepish manner. They held eye contact for another moment before she seemed to gather herself and addressed the new additions to the table. “And how are you two?”

“Uh…” Sam stammered, taken aback by the exchange he had just witnessed. “We’re good, thank you.”

“We just got back from a safari.” Jack announced, either oblivious of the sudden tension surrounding the group, or looking to break it.

“Ahh, at the Africam Zoo?” She asked, looking intrigued.

“Yeah, actually.” Sam nodded.

“My uncle is one of the tour guides there. I don’t think he was working today, though.”

“That’s so cool!” Jack exclaimed, bouncing in his seat. “Does he get to hold Berta whenever he wants?”

“The python?” She questioned, shaking her head and smiling. “ _ Dios mio ,  _ no. He is terrified of snakes.”

“Are you?” Cas asked innocently, taking a sip of his drink.

“No,” she replied, turning a now overtly flirtatious look on him. “Especially when I’m with someone who knows how to handle them.” She leaned towards him a bit, lowering her voice to a conspiratorial whisper. “If you know what I mean.”

Dean choked on the first tentative sip of his drink, nearly spewing pink liquid all over the table.

Cas raised an eyebrow at him and Sam slapped him roughly on the back, looking at him with concern.

Isabel flipped her long hair over her shoulder and turned her attention back to Sam and Jack.

“What do you boys want to drink?”

She jotted their drink order down quickly and gave them a little smile before leaving the table again. As soon as she was gone, Jack turned to Cas with wide eyes.

“Was than an innuendo?”

“Yeah, Cas- what was up with that?” Sam asked as he watched Isabel disappear to the interior of the restaurant.

“Casanova over here decided he’d start flirting with waitresses.” Dean replied, plastering a smile on his face that looked just a little too forced.

“She seems… into it.” Sam stated, giving Cas a grin. “Nice, man.”

Cas blushed a little and returned his focus to his menu. “She seems very nice.”

“And pretty!” Jack added.

“You should ask her if she wants to do something later. After she gets off work.” Sam suggested.

“Whoa- I don’t know about that.” Dean insisted, brows raised high with worry. “I mean- you don’t wanna come on too strong, man. That’ll just push her away.”

“Well, what’s the point of flirting then, Dean?” Sam questioned, giving him a confused look.

“I don’t know.” Dean replied, looking slightly hysterical as he threw his hands in the air. “Just for the experience?”

“Dean’s just jealous.” Cas offered, not even glancing up from his menu.

“Wh- what? I am  _not _ jealous.” Dean insisted, hands smacking down on the table with just a little too much force.

“Dean, I know you were trying to flirt with her first.” Cas explained, looking across the table at his friend. “I’m sorry- I didn’t mean to ‘steal her from you’.”

Sam threw his head back in boisterous laughter. “So- you struck out and Cas swept her out from under you, then? Classic, man.”

Dean glared at his brother and muttered angrily under his breath as he buried his face in his menu. Before long, Isabel arrived back at their table with Sam and Jack’s drinks and took their food order, but not without another significant bout of flirting with Cas. Dean squirmed uncomfortably in his seat whenever she returned to their table, and refused to communicate with her beyond grunts and nods. She obviously assumed he was embarrassed by the entire ordeal and stopped trying to talk to him, but she did engage in light conversation with Sam and Jack. She told them about other interesting tours in the area, and what she enjoyed doing the most as a local; she was, overall, an entirely pleasant person. So, when Sam managed to convince Cas to stay behind when they were finished and ask her to get together, they were all slightly baffled by Dean’s reaction.

“Whoa, just- hold on a minute, alright?” Dean demanded, half rising out of his seat before plopping back down.

“What is the issue, Dean?” Sam asked, shaking his head at him. “Aren’t you usually the one pushing for this? ‘Teachable moments’ and all that?”

Dean pursed his lips and ran a hand through his hair. “Yeah, yeah- of course.” He stammered, refusing to meet any of their questioning stares. “I just- you’re kinda jumpin’ in with both feet here, huh?”

Cas shrugged. “I don’t foresee many more opportunities for me, Dean.”

Dean’s eyes flicked up to his. “What do you mean by that?”

Cas looked away, ran a hand through his wild hair. “I… don’t get out much, back home. And it’s not like I’ve had many people show interest in me in the past, is it?”

Dean looked slightly taken aback by this. They had run into their fair share of people, supernatural or otherwise, that had unabashedly commented on Cas’ good looks. Meg had been more than interested and had loved him in her own way- as much as a demon was capable of loving anything, really. And April- well, she  _ had _ outright tricked him in the skeeviest way possible. Dean had to admit that on the job was not the best way to meet someone, which was why he stuck to hook ups he’d find in bars. And Cas had been missing in action since he lost the last of his grace- admittedly because Dean was anxious about bringing him along on hunts when he was now forced to rely on something other than his angel mojo to get him by. He could get hurt, and now he wouldn’t be able to heal himself. So, maybe Cas was kinda right. But that didn’t halt the unsettling feeling that was burrowing inside of Dean’s gut. Cas had never shown interest in anyone before either, so why now? 

“Alright-” Dean spoke finally, voice as tight as his smile as he rose from the table with Sam and Jack. “Good luck, man.” 

Cas gave him a strange look but nodded at him as they walked away, leaving him alone at the table. Sam, Jack, and Dean walked to the other end of the patio, waiting for him by the exit and watching surreptitiously as Isabel returned to their table, smiling shyly at Cas. They talked for a moment before she pulled a notepad out of her serving apron, wrote something down, and tore the page off to hand to Cas. He looked down at it, gave her a charming smile, and tucked the paper into his pocket. 

“So- what did she say?” Sam demanded as Cas approached them, blushing faintly.

“She said she can’t tonight, but after work tomorrow. She’s going to meet me at the bar down the beach around nine… she gave me her number.”

“Alright, man!” Sam clapped him on the shoulder, pulling him into a sideways hug. “Wow, who would have thought you’d be so suave. Picking up chicks on your first try! Crazy- right Dean?” Sam turned to his brother who was lagging behind them a bit as they began walking back to their hotel. 

“Oh, yeah,” Dean replied, close lipped smile stretching across his face. “Totally awesome.”

Sam cast him a concerned look over his shoulder but disregarded him to continue congratulating his friend, which quickly evolved into giving him pointers for his date.

“You wanna make sure to get there early, Cas. Maybe bring her a flower or something- not like a whole bouquet, that’s a little too formal- but something you find on your way there that you can tuck behind her ear… yeah, very romantic.”

Dean rolled his eyes sullenly. “Holy shit, are you a literal woman?”

Sam pursed his lips, turning to glare at his brother. “Just because your idea of romance involves burgers and shots of tequila-”

“Oh, please!” Dean spat, scoffing as he sped up to walk beside Sam. “I did live with a woman for a whole year, you know? I can be romantic.”

“You played house dad, Dean.” Sam responded, shaking his head. “Did you ever take Lisa out on a real date?”

Dean started to yes- he really, really wanted to say yes- but as he thought on it, he couldn’t remember a single instance where he had. Not even out for a nice dinner or a movie with just the two of them… shit- maybe he was as romantically impaired as Sam was suggesting. In his defense, he never really had the occasion. Sure, he lived the domestic life with Lisa for a while but that relationship required exactly zero effort on his part. He had been incapable of giving her anything else. Most of his other relationships never lasted longer than an orgasm, or two.

“That’s beside the point,” he declared, leaping around the subject. “That shit doesn’t sound like Cas. He should just be himself, chicks can tell when you’re being inauthentic.”

“That’s true…” Sam replied, looking thoughtful. “If you don’t feel comfortable with it, then don’t do it. That goes for a lot of things in a relationship, really.”

Cas nodded, tilting his chin as he considered his friend’s words. “I feel as if I am not socially adept enough to attempt what you suggested with flowers, Sam. I’m afraid I would come off as incredibly awkward.” Cas paused as they reached the sidewalk in front of their hotel, shifting nervously between his feet. “In fact- I’m not sure if I feel comfortable being entirely alone with her. Would you guys mind coming as well, to make it more of a group outing? I feel as if this would take some pressure off of me.”

“What?” Dean chuckled as he stepped onto the sidewalk beside him, shaking his head. “We are not coming on your date with you, man.”

“Well…” Sam began, looking to his brother. “It’s not like they’re meeting somewhere private. I mean, we could go to the bar and hang out. Not necessarily with them, but just to be there for moral support, you know?”

“Oh, no.” Dean shook his head sharply, eyes going a little wild. “I’m not doing that. Cas is a big boy, he doesn’t need us to hold his hand. Right, buddy?” He turned imploringly to Cas, only to find him giving his best impersonation of Sam’s puppy dog face. 

“I would appreciate it, Dean. If I feel as if I am making the situation awkward, it would be easier knowing you guys could step in to help me if I needed. Just in case.” 

“Oh my god.” Dean rubbed his forehead viciously, willing away the formations of a killer headache. “Fine. Whatever. But if one hour goes by and you two seem to be doing just fine, then I’m leaving.” 

“That’s fair.” Cas conceded.

“Great!” Sam exclaimed, bounding past them all as he continued on their way to the hotel. Cas trailed after him, looking pleased with himself. Jack hung back a beat with Dean, face drawn in concern. He was about to say something when Dean met him with a tight, closed off expression.

“Come on.” Dean tipped his head in the direction of the other two and Jack hesitated again before reluctantly following after him. 

They didn’t hang around their hotel room for long, as Dean was pacing the space anxiously, feeling as if he was about to climb the walls. They made it half an hour before Sam was ushering him out of the hotel room and back down to the beach. Jack tagged along with them, but Cas decided to stay behind. He wanted to read the book he had brought along and wasn’t big on reading outside, especially when the sun was so strong. He moved his bag out to the living room- it was his turn to sleep on the couch that night anyways- and curled up in a large chair facing the floor-to-ceiling window view of the water. 

Before he knew it, several hours had passed and the sun was setting, casting long shadows across the room. He had nearly finished his book when Sam, Dean, and Jack got back to the room, looking happy but drained from the day spent in the sun. 

“I’m beat.” Sam spoke through a wide yawn, stretching his arms high above his head as he threw himself onto the couch.

Dean glanced around as he came to sit beside his brother. “What were you doing up here all this time, Cas?”

Cas unwound himself from the plush armchair and held up his book.

“On The Road?” Sam read the cover in bemusement. 

Cas shrugged, looking down at the worn pages of the book. He had found it in a used bookstore not long after he became fully human again. Dean and Sam had taken him to a local flea market to load him up with his own clothes, and he had wandered into the shop next door. He had heard of most of the titles he came across while weaving through the crooked shelves, but this one had stood out to him. Metatron’s personal analysis of the novel had echoed through his head, less pronounced without his grace, and he bought it on a whim. It was proving to be much more intriguing than what Metatron had glossed from it- or, perhaps such things were simply slipping further from Cas’ mind since he lost his grace, harder to hold now without the capacity for infinite knowledge. 

“I’ve always found books to be an easier insight into the human psyche than I get by simply interacting with others and trying to make sense of it.” Cas laid it back into his lap and folded down the top corner of the page he had stopped on. “There’s something desperate and raw about books that people shy away from in their everyday lives.”

“That’s because people don’t write stories about boring, everyday shit.” Dean commented.

“That’s not true.” Cas replied, setting his book on the coffee table and resting his elbows on his knees. “It’s not about what an author chooses to write about, it’s about the meaning they put behind it.”

“Alright, you’re losing me now, man. I don’t go in for all that deep shit.” Dean waved a dismissive hand.

Sam rolled his eyes and punched his brother’s shoulder. “Okay, Vonnegut.” 

It wasn’t long before everyone retired to their respective rooms to sleep, eyes heavy and skin tinged pink and healthy from the sun. 

Dean only made it a few hours before he woke with a start; jolting up in his bed as the stiff hotel sheets bunched around his middle. He sat frozen for a moment, sweating and panting from a nightmare he couldn’t quite recall before throwing the covers back and shuffling to the kitchen for a glass of water. The living area was almost completely dark, except for a faint glow coming from the direction of the couch. Dean paused on his way to the kitchen, squinting in the low light.

“Cas?” He whispered, just loud enough to carry across the room.

Cas’ head slowly peeked over the back of the couch, confused and hair ruffled from laying down.

  
“Dean?”

Dean padded into the kitchen and filled a glass with water before going to sit on the opposite end of the couch. Cas bunched his knees so Dean could fit on the end, holding his phone against his chest and looking bewildered.

“Did you have a nightmare?” Cas’ deep voice pitched low in a concerned whisper.

Dean shrugged and took a long gulp of water. “What are you doing on your phone? It’s like three in the morning.” He deflected, gazing curiously at Cas’ hand clutching his phone.

“Uh,” Cas glanced anxiously from Dean to his phone before letting out a sigh. “Pornography.”

Dean choked. Water spilled down the front of his shirt and he swore quietly.

“What the hell?” Dean demanded, looking a little frantic and attempting to scoot further down the couch.

Cas narrowed his eyes in a half-hearted glare, reaching one foot out to shove at Dean’s leg. “It was your idea.”

“My idea?” Dean parroted, batting his foot away. “I don’t remember suggesting you get handsy with yourself in the living room at three in the morning.”

Cas pouted in frustration. “I was not ‘getting handsy’ with anything, Dean.” 

“Yeah, whatever you say man.” Dean replied sarcastically and made to stand up. “I’ll just-”

Cas sat up, resting his back against the arm of the couch and rolling his eyes. “For heaven’s sake, Dean- I wasn’t touching myself.”

Dean eyed him wearily but refrained from fleeing back to his room, waiting expectantly for an explanation.

“I was just,” Cas looked away and rubbed at the back of his neck. “You suggested earlier today that I watch it to… gain more knowledge of such human interactions.”

Dean sat dumbfounded as he racked his brain for the alleged conversation.

“Oh- you mean after that chick saw us at the market?”

Cas visibly relaxed. “Yes. You were talking about kinks… I still didn’t fully understand what you were referencing, so I thought I would do my own research.” He waved his phone for emphasis before setting it beside him on the couch.

Dean stared at the device for a minute, one stupid question echoing through his head that his half-awake mind apparently couldn’t help ask. “What were you looking at?”

“Uh,” Cas glanced nervously at his phone again. “I just searched ‘kinky’ and ‘porn’. I didn’t find anything illuminating… are some humans really sexually aroused by feet?”

Dean barked out a surprised laugh, covering his mouth to muffle the loud noise. “Unfortunately, yes.” 

“That is unfortunate.” Cas picked absently at a loose fabric on the couch. “Other things weren’t quite so disturbing.”

“Oh yeah?” Dean forced himself to lean back into the couch cushions and appear relaxed. “Like what?”

Cas swallowed audibly, keeping his eyes on the small space between them. “There was something about handcuffs… and another had two people with a third watching them.”

Dean went still and quiet for too long before forcing himself to give a slow, stiff nod. “Uh,” his voice came out rough, so he coughed. “Yeah that’s- that’s pretty standard stuff, I guess.” 

Cas fidgeted, glancing down at his hands in his lap.

Dean added, “So, no pizza man?” Tone light, trying to shake off the awkward tension permeating the air between them.

Cas looked puzzled for a moment before his eyes widened. “Oh. The pizza man.” And then, almost to himself. “That was good, too…” 

“What about it?” Dean blurted and immediately wanted to slap himself. He should really just shut up.

Cas contemplated his answer, absently rubbing at his knee. “The way the pizza man interacted with the babysitter.”

“You mean, like… the degradation?” Dean’s throat was very dry.

“I suppose. Is that odd?”

Dean rubbed his sweaty palms on his pajama pants and took a long drink of tepid water. “Nah. Everyone likes something different.”

Cas sat up further in interest and drew his legs under himself. He paused and bit at his bottom lip nervously, before taking an encouraging breath. 

“What do you like?”

“Me?” Dean nearly squeaked, heart rate ratcheting up and heat gathering in his face. He rolled the nearly empty glass of water between his hands. “I’m a people pleaser. Don’t really have anything specific of my own. I like doing what makes other people feel good, I guess.” 

Cas rolled his eyes affectionately. “That sounds about right, I guess.” 

Dean flashed him a twitchy grin. “So, you feel like you’ve got a better grasp on the concept, then?”

Cas started to nod and hesitated, eyes flashing to Dean who froze at the look in them. His features had darkened, something hot and dangerous slipping over them. Dean got caught up in it, openly staring at his friend’s mouth as it fell slightly open, wet tongue sliding over his lips. Dean squirmed, hands unconsciously clenching, and then Cas blinked and the heat was gone. 

“Uh- yes. Thank you, Dean.” 

Dean forced an unconcerned shrug and stood up a little too quickly. “I didn’t really do anything, man.”

“You’re the one who suggested I look into it.” Cas replied, blinking up at him with wide, guileless eyes. “And you’ve been open enough to discuss it with me just now. I appreciate it.” 

Dean blushed, hoped Cas wouldn’t notice in the dim light. “Yeah, uh, no problem, buddy. I’m just- gonna try to get back to sleep now. See ya in the morning.” 

“Goodnight, Dean.” Cas grabbed the thin blanket Jack had dug out from one of the bedroom closets earlier that night from off the floor beside him. He pulled it up to his chin and laid back on the couch, closing his eyes as he shifted into his pillow. 

Dean returned quietly to his room after setting his glass in the kitchen sink and pausing briefly to glance at Cas curled up under his blanket. The couch looked comfortable enough, but Dean couldn’t help the thought that he’d probably sleep better in a bed, purposefully ignoring that his brain conjured  _ his bed .  _

When he pulled his own covers over himself and laid down, he found he couldn’t close his eyes. He deliberately traced random patterns in the ceiling above him, stubbornly and stupidly keeping his mind from drifting to Cas. He never managed to fall back asleep. 

  
  


**Notes for the Chapter:**

> “Disculpe mi amigo, siente la necesidad de ejercer su virilidad alrededor de mujeres atractivas. Si quieres enseñarle una lección, tráele la bebida más frutal que tengas. Tendré lo mismo.” ---- Excuse my friend, he feels the need to exercise his manliness around attractive women. If you want to teach him a lesson, bring him the fruitiest drink you have. I'll have the same.
> 
> gilipollas ---- loosely translated as douchebag
> 
> bombón ---- literally translated as like chocolate, but is a term of endearment for someone sweet


	4. Chapter 4

“Chichen Itza?”

“Bless you.” Dean mumbled, trudging past his brother on his way to the kitchen. He scrubbed a hand over his face, lack of sleep making him groggy and disjointed. His feet drug across the tiled kitchen floor and he sighed in satisfaction when he spotted a full pot of coffee perched under the dispenser. 

“I think you would prefer Tulum.” Cas ignored Dean’s comment, pointing to one of the pamphlets Sam had laid before him on the kitchen island. It boasted a tall stone structure perched at the edge of a cliff that looked like it would provide picturesque views of the ocean. “It’s a smaller site, but more scenic. Also, there’s a park nearby that Jack may find enjoyable.”

Jack perked up over his plate of toast and mangoes. “A park?” 

“Oh, I see.” Sam plucked another pamphlet from the pile that featured images of families ziplining and snorkeling in clear blue waters. “Xel Ha.” 

“Do they have dolphins?” Jack’s stool scraped across the floor with a grating noise as he leaned over Sam’s shoulder. 

“Doesn’t look like it. Just fish and turtles.” 

Jack’s face fell a bit, but he looked over the other images with interest. “I think this would be fun. I choose this one.” 

“Well, you guys have fun.” Dean sipped his coffee apathetically, letting the warmth of it soothe his tired body. 

Sam shot a look at him over an image of some guy sleeping in a hammock. “You’re not coming?”

“Nah. I’m gonna work on my tan, drink some beers.” He let a lazy smirk curve around his coffee mug. “Maybe take a siesta.” 

“Isn’t that pretty much what you did yesterday?” Sam chastised, lips pushed into a thin, disapproving line.

“What? No- I was teaching Cas how to swim.” He countered, looking offended. “It was very labor intensive, hardly any time for relaxing.”

Sam continued to fix him with a disappointed stare, brows drawn low and wrinkled with irritation.

“You should come, Dean.” Cas stated casually, carefully pouring himself a cup from the steaming carafe. “The Mayan ruins really are something to see.”

“You’re going?” Dean leaned back against the counter, watching Cas as he fit the coffee pot back onto the warming plate with a click. 

Cas looked up at him through the steam slowly rising from his mug, eyebrow slightly quirked. “I wouldn’t miss a chance to see them again.” 

“Come on, Dean. We’re going to be gone like all day- if you don’t come we’ll hardly see you.” Sam implored, palms laid out flat and pleading on the granite counter. 

“Also, there’s a tour option that includes an open bar.” Jack entreated, waving a hand over the back of the pamphlet. “And it looks like they give out free margaritas at the park.” 

“An open bar and free margaritas? God, I love this place.” 

“So you’ll come?” Sam asked, looking hopeful.

“Yeah, yeah. I’ll come.” He rolled his eyes and drained the last of his coffee with a loud slurp, tipping the cup all the way back, and placed it carefully in the sink. 

“Great! The bus leaves at eight. We should get going.” Sam declared, rubbing his hands together in excitement.

“Eight?” Dean spluttered as he glanced at the microwave clock. “That’s in like thirty minutes! I haven’t even had breakfast.” 

“You had coffee.” Sam commented dryly, raising from his stool.

“That’s not breakfast.” Dean snapped, glaring at the broad expanse of his back of his walked away. 

“They have food on the tour.” Jack informed, following Sam’s lead as they disappeared into their rooms to change. 

Dean looked down at himself, still dressed in nothing but a robe and a pair of boxers. “Shit. I wanted to take a shower today.” He mumbled, mostly to himself. “I didn’t wash that ocean smell off last night.”

Cas wrinkled his nose and wrapped his hands tighter around his coffee mug. He was already fully dressed in a t-shirt and shorts, hair soft and face clean-shaven. “How could you stand to sleep like that?”

Dean scoffed, crowding into his personal space a bit as he tipped his hip against the counter. “I slept dirtier than that before, Cas.” And then immediately flushed a hot, bright red at his phrasing. 

Cas raised an eyebrow, lips pinched together to hold back his laughter. “Right.” 

“I’m just gonna- go get dressed.” Dean motioned awkwardly towards his room and stumbled over his feet on his way. 

They arrived at the tour bus just a few minutes before eight. Luckily, the early morning tour they had opted for was obviously not the busiest of the day, leaving several seats for them to crowd together on. The interior of the bus was spacious and designed somewhat like those party buses people rent out in the states for bachelorette parties and twenty-first birthdays. Instead of the standard rows of seating, bench-like seats lined the walls on either side, leaving the middle completely open. The back wall was lined with bottles secured behind a railing and a large, built in cooler filled with a mixture of fruity cocktails and beers, as well as water and bottles of coke. 

“Alright!” A voice called their attention to the front of the bus, just as the four of them had settled in. “Who’s ready to have fun?”

Standing at the open entrance of the bus, an official ‘Tulum Tour Guide’ shirt stretched over his distinctly muscled chest and fixing the crowd with a gleaming smile, was a tall man with smoky brown eyes. There was a scattering of sleepy applause from the tourists- most looked like they were still waking up or fumbling through hangovers from the night before. 

“We are going to leave in just a few minutes here, guys! I’m just going to go over a few quick things before we depart.” He paused here, as if waiting for some sort of reaction from the crowd but they simply stared at him expectantly. “Okay- first, the drive from Cancun to Tulum takes about an hour and forty five minutes-” 

“Holy shit.” Dean blurted in surprise and immediately covered his mouth in embarrassment. 

The tour guide turned to him with a frown, but his expression lit up when his eyes cast over him. 

“Sorry,” Dean apologized, looking sheepish. “Just didn’t realize it would take that long.”

“That’s fine,  _ pecas. _ ” He gave him a wink that turned up the side of his face before continuing his speech. 

“Pecas?” Dean repeated quietly, turning to Cas. “What the hell does pecas mean? Is that guy insulting me?”

Cas was looking at the man with an unreadable expression. “It means ‘freckles’.”

“Freckles?” Dean looked up at the guy again. He was addressing the group at large, but when he caught Dean’s eye he winked again. “Oh.” Dean looked down quickly, occupying himself with a scuff on his boot. 

“So, everyone help yourselves to whatever drinks are in the back. There are also snacks, if you are hungry.” He motioned to the back wall as he wrapped up his speech. “We should be leaving in just a few short minutes!” 

Dean bolted for the back of the bus the minute he was done talking. He had grabbed a bag of chips and was reaching for a beer when he felt someone sidle up behind him. 

“Hello.” The tour guide greeted, flashing him an impossibly white smile. “My name is Dante.” He stuck out his large, smooth hand, looking expectantly at him.

Dean glanced at his hand and back up. “Dean.” He grasped it quickly and gave one firm shake, smile going a little gooey- the guy was… very attractive. 

Dante took a step closer, eyes flickering over Dean. “It’s a little early for cerveza, hm?”

“Yeah, I don’t know what that means.” Dean replied with a smirk, falling way too easily into the flirtatious atmosphere. He definitely knew what cerveza meant- was probably one of the only spanish words he actually knew. 

“Beer.” Dante elaborated, running a tongue over his bottom lip and pointing at the bottle in Dean’s hand. 

“Ah,” Dean glanced down at his fingers wrapped around the neck of it and gave a small shrug. “Well, you know what they say. It’s five o’clock somewhere.” 

Dante looked puzzled for a moment before his face split into a charming smile. “Yes, you are right.” He stepped around Dean to reach into the cooler. “Might as well start the day off right.” And then his tone dropped, settled into something a little more honest and less put on. “These tours can become very exhausting.” 

“There you go.” Dean gave him a crooked smile and clinked their glasses together. “You make this trip every day?”

Dante took a long pull from his bottle and shook his head, bumping his hip onto the cooler as he leaned against it. “No, just Monday, Wednesday, and Friday. Other days Carmen is here.” 

“Must be a pretty long day for you.” Dean commented, drinking from his own bottle and attempting to ignore the way the guy’s shirt was riding up over his waist, revealing a strip of tanned skin on his lean stomach. 

Dante smirked, caught his eye. “Sometimes it is made better by the customers.” 

Dean shifted awkwardly on his feet and glanced around the bus. Everyone seemed to be preoccupied with their own group, waiting for the bus to take off. He glanced back up at Dante and swallowed loudly- the guy was definitely trying to hit on him and it had been, well, a  _ really _ long time since anyone had done that. And even longer since a guy had. Dean never did well channeling the same flirtatious atmosphere he was able to produce around women with men- really, he became a bit of a blundering mess when guys hit on him. 

“You get a lot of, uh, interesting customers?” Dean almost cursed at his pathetic attempt, but something in his tone must have registered. Dante’s deep brown eyes suddenly lit up and scanned thoughtfully over Dean’s face.

“None so interesting as you seem to be.” 

Dean let out a nervous chuckle, gripped his beer bottle a bit tighter, and glanced around the bus again. This time, he caught Cas’ eye. He was looking between Dante and Dean with a shrewd expression. Upon meeting Dean’s eyes, he raised a questioning eyebrow. Dean gave him a barely perceptible shrug. 

Dante took a noticeable step back as he caught their nonverbal exchange. “Your, uh, friend?” He asked, tilting his head curiously in Cas’ direction. 

Dean nodded. “Uh, yeah. That’s my friend Cas.” He pointed him out and gave him a wave for emphasis. Cas replied with an annoyed eye roll. “My brother Sam.” He pointed to the right of Cas. Sam waved back with a bit of an eyebrow raise. “And our… nephew, Jack.” Jack gave an innocent grin and Dante waved at all of them in turn, but seemed to keep a questioning eye on Cas. 

“Your… friend, he seems a little tense.”

“Cas?” Dean questioned, glancing over at his grumpy face again. Dean tilted his head slightly, as if considering. “Nah, that’s just how he is.” 

“He should loosen up a little. Like you.” Dante suggested, pointing towards Dean’s beer. 

“With cerveza?” 

“Yes!” Dante nodded enthusiastically. “I will get him one.”

Dean shrugged and followed Dante back over to their group. He handed a cold bottle out for Cas, who stared at it with distrust before Dean prodded his shoulder. 

“Dude, just take it.” 

Cas sighed and took the bottle, but didn’t open it, just held it loosely between his knees as he continued to stare warily at Dante.

“So, you are all here for family vacation?” Dante questioned the group of them. 

Sam nodded, clapped Jack on the shoulder. “Yeah, we thought it would be a good way to expose Jack to some new cultures.”

Dante nodded and smiled warmly. “That is a great thing, many people only come here to get drunk and lay on the beach- they have no idea what kind of history this country has.”

Dean gave a strained laugh, rubbing the back of his neck and ignoring the amused smirk Sam shot at him. 

“Well, this is only our second day here, but Jack and I took that safari tour yesterday. It was incredible.”

“Are you interested in dolphins at all?” Dante asked, eyeing Jack when he visibly perked up at the mention. 

“Yes, actually.” Sam replied, patting Jack’s shoulder fondly. “Jack is dying to see dolphins.” 

“I know a really great place; they are a good price, and not very well known so it is not as busy as other places. I can give you more information on them later.”

“That would be awesome, thank you!” 

“Great!” Dante took one more drink from his beer before setting it down. “Well, I guess I should get to my job. I have to make my rounds before we arrive; make sure everyone has what they need and are briefed on the schedule for the day. I will talk to you all later though.” He promised, departing from the group and shooting another wink at Dean, patting him on the shoulder as he walked away.

“He seems nice.” Sam commented, turning a rueful smile on his brother. “He was a little friendly with you though, Dean.” 

Dean’s face immediately caught on fire, only getting worse when Cas replied, “He was interested in Dean.”

At the blank look he received from Sam, Cas added, tone sharp and short, “ _ sexually _ .”

Sam let out an undignified snort. “What?” 

Jack just shrugged, looking between them in mild interest. “Is that a problem or something?” 

“No, it’s not a problem.” Dean replied, voice stony as he glared at his brother. 

Sam abruptly stopped laughing and cast an apologetic smile towards Jack. “Yeah, uh, sorry. No, there’s no problem with a guy being interested in another guy, Jack. I was only laughing because the other guy is Dean.” 

“I understand the concept of homosexuality, Sam.” Jack replied. “I just don’t understand why it’s so funny when it has to do with Dean?”

“Can we stop talking about this now?  _ Please?”  _ Dean hissed, now red up to his hairline and looking like he was about to pass out. 

“But Dean, aren’t you-” Jack was interrupted by a loud groan from Dean. 

“Seriously.” He demanded, hand slicing through the air in a sharp gesture, leaving no room for discussion. “That’s enough.” 

Jack closed his mouth but continued to stare thoughtfully at his hands resting in his lap. 

The ride was spent in a slightly uncomfortable silence between the four of them; Dean drinking steadily through two more beers, the tight tension riding in his shoulders ebbing halfway through the second. Sam seemed to be deep in thought, staring out the window with glazed eyes as Jack fidgeted next to him, uncomfortable on the hard bench seat. Cas had his head tipped back against the window, eyes closed and headphones in his ears. He was pressed up against Dean’s side and the more Dean drank, the less aware of it he became. Soon, he was practically leaning against him, head turned as he watched him let out a deep breath, eyes closed and looking peaceful. Dean nudged him with his knee, drawing his attention slowly. 

Cas peeled an eye open and looked over at his friend. Dean made a gesture with his hand, silently asking Cas to hand him one of his ear buds. 

Cas scoffed. “You hate my music.”

“Better than sitting here in silence.” Dean shrugged, his shoulder brushing against Cas with the motion.

Cas resigned, handing him one of the buds. Dean popped it in his ear and immediately recoiled.

“Aw, seriously, man?” 

Cas rolled his eyes and made to yank it out of his ear, but Dean held up his hands in a placating gesture. “Sorry, sorry. I just can’t believe you were looking so peaceful while listening to rap music. Thought it was gonna be Mozart or something.”

Cas gave him a look and let his head tip back onto the window again, pointedly closing his eyes and folding his hands in his lap. Dean grimaced to the sound of the harsh beat and disjointed lyrics, but copied his friend’s posture and tried to relax. 

Dean didn’t open his eyes again until the bus started rolling to a stop.

“Alright, everyone!” Dante clapped his hands together once as he stood at the front of the bus. “We are arriving at Tulum. When we come to a full stop, we will all exit the bus, and follow the path up to the stone buildings. The site gets rather busy this time of day, so just look out for me in the crowd and try to stick together!” 

As he finished, the bus came to a stop and the door squeaked open. Dante motioned for everyone to follow him as he stepped off and began walking in the direction of several tall and crumbling stone buildings. The air had grown sticky over the two hour drive, no longer the breezy warmth of mid-morning, and Dean could already feel sweat beading along his forehead. 

“Just this way!” Dante called over his shoulder as everyone filed off the bus behind him. Once they entered the actual city, he began motioning towards the first building they would visit. They climbed a few steps, where it was less crowded, and he began to recall what was obviously a scripted history of the structure. 

“This is the House of the Halach Uinic; every Mayan city was ruled by a halach uinic. They served as the high-priest and were revered. This is one of the better preserved buildings, as you can see. Now, if you look over here…”

Dean’s attention began to wander as he looked over the other buildings around them. They didn’t seem like anything too special to him, but Sam and Jack seemed to be eating it up. Cas appeared to be lost in his own thoughts, staring at Dante with a far off look in his eyes that didn’t speak of concentration on what he was saying. 

“You really been here before, Cas?” Dean asked, bumping him with his shoulder to gain his attention. 

Cas blinked several times and looked over at Dean. 

“Ah, yes.” He replied, pointing across the way to the largest building situated on the edge of a cliff over the ocean. “That is the most interesting building. The views of the ocean there are incredible.”

Dean followed his gaze. There wasn’t much to see from their current vantage point. 

“You ever come here before it was ruins?” 

Cas shook his head. “No. I wasn’t stationed on Earth much before I met you. I only came on strict orders with little room for sightseeing. Though, I did try to slip away if I ever got the chance.” Cas flashed him a mischievous smile. 

“You were always a rebel.” Dean flashed him a smile that was all teeth and a little teasing. “Don’t know why you blame it on me.”

Cas squinted and tilted his head, gaze focused intently on Dean. “Perhaps.” He replied after a few moments. “But without you, I never would have had the courage to go directly against my superiors. I had an inkling of free will; I was always different from other angels.” Cas’ voice was painfully nonchalant as he added, “But, before I met you there was no one who could have made me fall the way you did.”

Dean blinked several times and looked away, hiding his face. Sometimes Cas was dry and blunt in a way that Dean didn’t think he’d ever grow fully used to. 

“Alright, you guys can look around up here for a few minutes, and then we will move on to the next building.” Dante declared loudly, grabbing their attention once again. 

“Hey Dean, Cas!” Sam called from the top of the stairs, holding his phone up. “Come up here so I can take a picture!”

Dean groaned. “He’s such a girl.”

Cas smiled fondly at Sam’s excited face. “He enjoys these things. Just humor him.” 

“You know I will,” Dean replied, rolling his eyes as they trudged up the last few steps. “I just have to give him shit for it first. It’s my job.” 

“Okay, go move over here. Yeah, in front of the entryway.” Sam instructed as Jack wormed his way in between Dean and Cas. They each threw an arm over his shoulders and put on a smile. Jack could barely stand still as he was trying to look around and soak in every detail he could. 

“Okay, that’s a good one!” Sam declared, looking down at his phone. 

“Do you want me to take one of you?” Jack offered, holding a hand out for his phone. 

“Yeah, thanks Jack!” Sam handed his phone over and came to stand beside Dean and Cas. Instead of putting their arms over him, his height advantage made it easier to put an arm around each of them. 

“Okay, smile!” Jack prompted, and Dean screwed up his face and stuck out his tongue at the last moment. 

When Jack showed Sam the picture he sighed but let out a small chuckle. 

“Dean, what the hell?”

“What?” He asked innocently. 

Sam just rolled his eyes and pocketed his phone. Soon after, Dante was calling for their attention again as they made their way to the next building. It went much the same as the last as he pulled out some rehearsed facts and then gave them a few minutes to explore and take pictures. This continued for the next few buildings as well, until they reached the final and largest one. 

“This is the main attraction of Tulum.” Dante declared as they began climbing the steep steps. “ _ El Castillo _ or the Castle was used as a rudimentary lighthouse.” He took a moment once the group reached the top to let everyone look around before pointing to the very top of the pyramid, where two small squares were carved from the surrounding stone. “Merchant boats would use those windows as a guiding point as they sailed in. If they could see daylight through both of them, they would be clear of the reef that lies below the water here.” He gestured for everyone to step forward further, until they could see over the edge of the building and down the side of the cliff. 

Dean whistled lowly, shielding his eyes from the sun as he looked over the clear blue water. “You weren’t lyin’, Cas.”

“I rarely lie, Dean. Especially about such trivial things.”

Dean smiled and turned to Cas to make some smartass remark, but it died in his throat. Cas’ face was washed in the sun, hard angles of it cast like marble in the light and his eyes like mirrors reflecting the ocean water back at him. He looked ethereal, standing on the precipice of the remains of an ancient building and Dean was struck, not for the first time, with the reminder of what Cas really is, or was. For a moment, he couldn’t breath. That space of time between one breath and another stretching on until he thought it wouldn’t come. Something inside him ached, not in any particular place but an all over, under the flesh of his skin and carved into his heart kind of ache. 

He dragged a slow inhale as he turned away from Cas, back towards the crowd of people that were milling around behind them. Looking away from him it was easier to snuff out the feeling, but it lingered like an aftertaste. He caught Sam’s eye and waved him over. 

“Hey, man.” Dean motioned between Cas and himself. “Will you take a picture of us?”

Sam smiled brightly at them. “Yeah, of course! One with the water behind you?” 

Dean nodded and waved Cas to come closer to him. He let a wide smile stretch over his face and wrapped an arm behind Cas’ printed shirt, pulling him in by the waist. Cas made a small, surprised noise but let himself be pulled in. He leaned against his side and Dean tugged him just a bit closer, until he fit neatly against him. 

“Okay, smile!” Sam prompted, holding his phone up to get a good angle. “Oh, I like that one.” He declared, bringing his phone closer to his face to look at it. 

Dean walked over and Sam held his phone out so he could see. It was a good picture- the two of them, standing close and grinning at the camera with the crumbling building and expanse of ocean behind them. 

“Uh, send that to me, will ya?” Dean requested, rubbing the back of his neck and avoiding his brother’s eyes. 

“Alright group,” Dante shouted over the crowd. “You all have one hour to walk around on your own. Meet back at the bus at noon!” 

The four of them dispersed to explore. Sam and Jack went to wander back through the smaller buildings, Cas took the flight of steep wooden steps down to the beach below, and Dean swerved off the main path a bit to sit at the edge of the cliff and admire the view. He was dripping sweat and wishing that he had snagged a bottle of water before leaving the bus when he heard footsteps behind him. Dean turned to look over his shoulder and saw Dante walking towards him.

“Hi, Dean. Do you mind if I sit with you for a bit?” He questioned, looking acutely nervous as he fidgeted with his hands.

“Go ahead.” Dean replied, motioning to the rocky ground next to him. He was perched on the lip of the precipice, feet resting on a jagged rock jutting out beneath him. He leaned his elbows onto his knees and let his arms fall between his legs. He could just make out the sound of the water lapping the shore below them, the hushed sound a background noise to the bustle of people behind them. 

Dante sat beside him, perhaps a bit closer than strictly necessary, but still far enough away so there was room between them. He planted his feet on the ground before him and wrapped his arms around his knees. 

“This is my favorite part of my job.” He spoke softly after a few minutes, eyes tracking the almost invisible line where the ocean meets the sky, their blues nearly identical. “No matter how bored I get with saying the same things over and over again each day, this place doesn’t get any less beautiful.”

“One hell of a perk.” Dean replied, voice a quiet and pensive thing as he let his mind wander. 

“So,” Dante started, rubbing his hands nervously against his khakis. He shifted a bit closer in the process and fixed Dean with a charming smile, drawing his attention fully in. “Usually I’m pretty good at this, but… for some reason, you are very hard to read.”

Dean felt an undeniable impulse to sway closer, a reaction that had been ingrained in him from a lifetime of one night stands and loneliness. It would be so easy to lean against him, brush their shoulders together, and hit him with his own flirtatious smile. The one that never failed to make girls blush, or help him talk his way past a security guard. However, he found himself hitting an invisible wall. This had happened to him before, more and more frequently over the past eleven years, to the point where it had been ages since he had flirted with anyone with any real intentions behind it. It couldn’t remember exactly when it began, but at some point he had incurred a nagging voice in the back of his mind that insisted it wasn’t right… a voice that may have sounded suspiciously like Cas. Dante was definitely attractive, and obviously attracted to him, but the thought of doing anything about it left Dean feeling ridiculously empty. Deep down he knew what- or more specifically who- he really wanted, but he had buried it under layers and layers of self deprecation and shame, and years of misunderstandings and miscommunications. The thought never let him though, just simmering under the surface of his skin, flirting around the edges of his consciousness and making it harder and harder for him to acutually enjoy pointless sex. 

“Look, I-” Dean started soft, clearing his throat of the emotions that had suddenly taken residence there, preparing to let him down easy.

“Ah.” Dante smiled knowingly and promptly drew back from his personal space. “I did misread. I am sorry.” 

“No, it’s not that, it’s just-” Dean stuttered, trying to find the words to explain himself.

“Oh.” Dante drug the expression out slowly, face lighting up in understanding. “It’s your friend, isn’t it? The grumpy one.”

Dean flushed, drawing his knees to his chest. “Yes- I mean, no. It’s just…” 

Dante placed a warm and comforting hand on his shoulder. “You do not have to explain.”

Dean let out a heavy sigh. “Yeah, thanks. It’s just- complicated.” 

“I know complicated.” Dante replied smoothly, moving into a reclining position and resting on his elbows. 

A gentle silence fell around them, not awkward, just understanding. Dean scanned the beach below them, spotting a familiar figure standing near the shore. He couldn’t make out much of his face from the distance, but he could tell Cas was looking up at them. Dean and Dante waved, but he turned away sullenly like he didn’t see them. 

Dante let a laugh bubble out of his chest. “He  _ is  _ grumpy though.”

Dean let a fond smile slip over his face as he watched Cas wade through the water, bending over to pull something out of the wet sand. “Yeah, sometimes.” 

“Well, we should probably start heading back. It’s almost time to meet.” Dante declared, pushing himself up. He held a hand out to help Dean and they made their way to the parking lot together. Sam and Jack were already there, taking refuge in the shade under a tree near the bus.

Soon, their entire tour group was accounted for and they piled back onto the bus. Cas seemed especially rigid as he sat next to Jack, trying to listen to him talk about what he wanted to do at the park, but finding his mind wander. 

“Will you go zip lining with me, Cas?” Jack looked up at him with big, wide eyes. Seemed like everyone learned how to perfect Sam’s puppy dog look. 

Cas grunted but didn’t reply. His eyes were fixed on nothing in particular and he appeared to be deep in thought.

“Cas?” Jack prodded him on the arm and he jerked slightly, blinking.

“What, Jack?” He very nearly snapped, his voice softened just enough around his name to make it less harsh. 

“Geez, what crawled up your ass?” Dean interjected, leaning around Jack to get a good look at him. Cas glared half-heartedly but didn’t say anything. 

The ride to the park went on in much the same manner; Jack letting loose a constant stream of excited babbling, Cas grunting or sighing in response and Dean watching him worriedly. Sam had a pair of earbuds in and was pointedly ignoring the lot of them. 

Xel Ha had some pretty cool amenities, but Dean had to confess that the hammock forest was probably his favorite. He spent most of his time swaying gently in the mesh ropes, relaxing with his hands under his head. Jack did convince Cas to go zip lining with him, somehow. He looked a little green and unsteady when they touched down, and immediately declared that he much preferred when he used to have his own wings. Sam spent his time doing a little bit of everything, as he wanted to get as full of an experience as possible. He didn’t zip line, but did watch Jack and Cas and spent a good amount of time snorkeling and swimming.

By the time they were being rounded back up to the bus, they were sagging in exhaustion.

“I’m beat.” Sam spoke through a thick yawn as he slouched in his seat.

“Me too.” Cas agreed, eyes heavy. Even Jack was more subdued.

“You’ve still got a date to make tonight, buddy.” Dean reminded Cas, wiggling his eyebrows at him. “You’re not going to have to cancel, are you?”

Cas frowned, looking down at his lap. “I almost forgot about that.”

Dean couldn’t help the small smirk that curved across his face. “I’m sure she’ll understand if you can’t make it.”

“Don’t be ridiculous.” Sam piped in. “We can nap on the way back and will still have,” Sam checked the time on his phone, it read four thirty. “Like three hours before you’re supposed to meet her when we get back. You’ll be just fine.” 

Cas tipped his shoulders up in a lethargic shrug, but didn’t argue. Dean felt his face fall and he slumped moodily back into his seat. 

During the two hour drive, only Sam had managed to catch any amount of sleep. His head tilted back on his seat and letting out huffy snores. Dean had wanted to mess with him so bad, but Cas had put the kibosh on any and all prank pulling on the sleepy moose. He snapped awake rather viciously when the bus came to a jerky stop. 

“We have arrived back at the resort!” Dante declared, taking up his spot at the front of the bus for a final time. “I hope you all had a wonderful time during the tour. I had a great time getting to know you all,” he caught Dean’s eyes briefly and flashed him a small wink. “And I hope you enjoy the rest of your stay here in Mexico.” 

The tourists immediately began shuffling to get off of the bus, all stopping to thank Dante at his perch by the door as they filed out, shaking his hand and smiling. When Dean approached, Dante gripped his hand a little tighter and used it to pull Dean into his personal space. He slipped a small fold of paper deliberately into the front pocket of his shorts and gave him a flirtatious grin.

“Just in case. I know you have ‘complication’, but that doesn’t mean you’re not allowed to have fun sometimes.”

Dean blushed and shoved his hand into his pocket, chasing the paper and fingering it nervously.

  
“O- okay.” He stammered and nearly tripped over himself as he exited the bus. 

“What was that?” Cas demanded, swooping in like a vulture as soon as Dean’s feet hit the concrete. He had been loitering near the bus, waiting for Dean while Sam and Jack made their way to the front lobby.

“Oh, uh- nothing.” Dean plastered a shaky smile on his face and brushed past him.

“He gave you something.” Cas stated flatly, following swiftly on the backs of his heels.

Dean’s hand unconsciously went for his front pocket again. “Yeah,” he took a deep breath, stealing himself. “He gave me his number, okay?”

Cas was silent for a moment, eyes squinty and head tilted as he regarded him. “You’re not going to keep it, right?”

Dean stopped walking, eyeing Sam and Jack through the revolving glass doors at the entrance. They were looking at them, just chatting idly with each other as they waited for Dean and Cas to catch up.

“So what if I do?” Dean snapped in a harsh whisper, rounding on his friend.

“But, Dean,” Cas’ eyes searched his face in confusion. “You’re- you’re not…” he floundered for the right words to say, but Dean understood.

“Well, what if I was?” He blurted, looking mortified even as the words left his mouth. He had never outright told anyone about this. He could feel his hands shaking.

Cas immediately reeled back, eyes widening in shock. “What do you mean? You’ve never-”

“Look,” Dean took a deep breath, trying to bring his frayed nerves back under his control. “Just because I don’t go around wearing a blinking pink and blue neon sign, doesn’t make it any less true.” He fidgeted with the hem of his shirt, tugging at it self-consciously. “It’s not, ya know… often. Chicks are easier and less of a risk considering the kind of places we frequent but,” Dean looked away with a shrug, heat crawling up his neck. “Every once in a while it’s just- something else might catch my eye.” 

Cas was acclimating to this idea quickly which, honestly, wasn’t really a surprise. He had said on more than one occasion that gender was a less than important trait in his personal opinion. It really didn’t matter to him- angels were genderless and he sometimes grew confused and frustrated at the importance humans seemed to place on notions regarding sexuality. It was mostly surprising because Dean seemed to go out of his way to make sure everything about him was typical alpha male. His car, his music, his clothes, and, though it had been a lot less frequent lately, his insatiable need for sex- with women, or so Cas had been led to believe until this very moment. 

“I’m sorry, Dean. I just- I had no idea. Obviously there’s no problem, I was just… confused.” 

Dean felt a strange sense of relief wash over him. He knew, realistically, there was a zero percent chance that Cas was going to care in the slightest but… this was still the first time he had ever openly talked about it. It was nerve-wracking. 

“Yeah. Thanks. Just,” Dean cast an anxious glance towards his brother, who was watching them with a growing sense of confusion as him and Jack continued to wait just inside the entrance. “Let’s just keep it between us, huh?”

Cas followed his gaze, his face pulling down in a frown. “Sam wouldn’t care, Dean.” 

“Yeah, well,” Dean bit his lip. “Even so, it’s not like anything will ever come of it. If he needed to know, I’d tell him. But this,” he tapped on the material of his front pocket. “Is not happening. So, nothing to tell.” 

Cas continued to frown. “If that’s what you want, Dean. I won’t say anything to Sam.” 

Dean let the tension in his shoulders fully subside and clapped Cas’ arm. “Thank, buddy. Now let’s go get you ready for that date, yeah?” 

Cas followed Dean inside at a slower pace, his mind racing. His date was the last thing he wanted to focus on right then, but he let Dean lead him past the rotating door and into the lobby. 

**Notes for the Chapter:**

> Let me know what you thought!


End file.
